HU189698B - Process for preparing 4-hydroxy-quinolines from quinolinones - Google Patents
Process for preparing 4-hydroxy-quinolines from quinolinones Download PDFInfo
- Publication number
- HU189698B HU189698B HU832157A HU215783A HU189698B HU 189698 B HU189698 B HU 189698B HU 832157 A HU832157 A HU 832157A HU 215783 A HU215783 A HU 215783A HU 189698 B HU189698 B HU 189698B
- Authority
- HU
- Hungary
- Prior art keywords
- tetrahydro
- quinolinone
- hydroxyquinoline
- chloro
- mmol
- Prior art date
Links
- 150000004331 4-hydroxyquinolines Chemical class 0.000 title claims description 4
- 238000004519 manufacturing process Methods 0.000 title 1
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical class C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 title 1
- 229930185107 quinolinone Natural products 0.000 title 1
- BUWPZNOVIHAWHW-UHFFFAOYSA-N 2,3-dihydro-1h-quinolin-4-one Chemical compound C1=CC=C2C(=O)CCNC2=C1 BUWPZNOVIHAWHW-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000000034 method Methods 0.000 claims abstract description 14
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 6
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 6
- 239000001301 oxygen Substances 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims abstract description 5
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical group [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 24
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 6
- 239000007864 aqueous solution Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims 1
- PMZDQRJGMBOQBF-UHFFFAOYSA-N quinolin-4-ol Chemical compound C1=CC=C2C(O)=CC=NC2=C1 PMZDQRJGMBOQBF-UHFFFAOYSA-N 0.000 abstract description 8
- -1 alkyl radicals Chemical class 0.000 abstract description 5
- 125000001424 substituent group Chemical group 0.000 abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 2
- 125000004432 carbon atom Chemical group C* 0.000 abstract 2
- WZKSXHQDXQKIQJ-UHFFFAOYSA-N F[C](F)F Chemical compound F[C](F)F WZKSXHQDXQKIQJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000001590 oxidative effect Effects 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 26
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 16
- 229910015900 BF3 Inorganic materials 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- HOLTZTRNTRXTNX-UHFFFAOYSA-N 7-chloro-2,3-dihydro-1h-quinolin-4-one Chemical compound O=C1CCNC2=CC(Cl)=CC=C21 HOLTZTRNTRXTNX-UHFFFAOYSA-N 0.000 description 10
- 239000007789 gas Substances 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- 238000004817 gas chromatography Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 7
- 229920006395 saturated elastomer Polymers 0.000 description 7
- 239000007858 starting material Substances 0.000 description 7
- XMFXTXKSWIDMER-UHFFFAOYSA-N 7-chloro-1h-quinolin-4-one Chemical compound ClC1=CC=C2C(O)=CC=NC2=C1 XMFXTXKSWIDMER-UHFFFAOYSA-N 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 4
- 238000000605 extraction Methods 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 239000012044 organic layer Substances 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 239000002253 acid Substances 0.000 description 3
- 239000008346 aqueous phase Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000001704 evaporation Methods 0.000 description 3
- 230000008020 evaporation Effects 0.000 description 3
- 239000012071 phase Substances 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- KQQQHTFGBIWLOD-UHFFFAOYSA-N 3-(3-methylanilino)propanoic acid Chemical compound CC1=CC=CC(NCCC(O)=O)=C1 KQQQHTFGBIWLOD-UHFFFAOYSA-N 0.000 description 2
- HXEWMTXDBOQQKO-UHFFFAOYSA-N 4,7-dichloroquinoline Chemical compound ClC1=CC=NC2=CC(Cl)=CC=C21 HXEWMTXDBOQQKO-UHFFFAOYSA-N 0.000 description 2
- VQWWRJNHWRYMLD-UHFFFAOYSA-N 7-methyl-2,3-dihydro-1h-quinolin-4-one Chemical compound O=C1CCNC2=CC(C)=CC=C21 VQWWRJNHWRYMLD-UHFFFAOYSA-N 0.000 description 2
- UDRWADJLLWWJOE-UHFFFAOYSA-N 8-(trifluoromethyl)-1H-quinolin-4-one Chemical compound C1=CC=C2C(O)=CC=NC2=C1C(F)(F)F UDRWADJLLWWJOE-UHFFFAOYSA-N 0.000 description 2
- WUQPOLBZMZKXOP-UHFFFAOYSA-N 8-(trifluoromethyl)-2,3-dihydro-1h-quinolin-4-one Chemical compound O=C1CCNC2=C1C=CC=C2C(F)(F)F WUQPOLBZMZKXOP-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229960001650 glafenine Drugs 0.000 description 2
- GWOFUCIGLDBNKM-UHFFFAOYSA-N glafenine Chemical compound OCC(O)COC(=O)C1=CC=CC=C1NC1=CC=NC2=CC(Cl)=CC=C12 GWOFUCIGLDBNKM-UHFFFAOYSA-N 0.000 description 2
- 238000004811 liquid chromatography Methods 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WHTVZRBIWZFKQO-AWEZNQCLSA-N (S)-chloroquine Chemical compound ClC1=CC=C2C(N[C@@H](C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-AWEZNQCLSA-N 0.000 description 1
- QRJMFMFNPROMBS-UHFFFAOYSA-N 1-chloro-2,3-dihydroquinolin-4-one Chemical compound C1=CC=C2N(Cl)CCC(=O)C2=C1 QRJMFMFNPROMBS-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- DCUHKPNLFWGSQE-UHFFFAOYSA-N 2-[4-(trifluoromethyl)anilino]propanoic acid Chemical compound OC(=O)C(C)NC1=CC=C(C(F)(F)F)C=C1 DCUHKPNLFWGSQE-UHFFFAOYSA-N 0.000 description 1
- JYYLQSCZISREGY-UHFFFAOYSA-N 2-amino-4-chlorobenzoic acid Chemical compound NC1=CC(Cl)=CC=C1C(O)=O JYYLQSCZISREGY-UHFFFAOYSA-N 0.000 description 1
- VGMMSBHENHMZBH-UHFFFAOYSA-N 3-(3-chloroanilino)butanoic acid Chemical compound OC(=O)CC(C)NC1=CC=CC(Cl)=C1 VGMMSBHENHMZBH-UHFFFAOYSA-N 0.000 description 1
- YHXKNYLHVMSFKC-UHFFFAOYSA-N 3-(3-chloroanilino)propanoic acid Chemical compound OC(=O)CCNC1=CC=CC(Cl)=C1 YHXKNYLHVMSFKC-UHFFFAOYSA-N 0.000 description 1
- AQKKRXMVSOXABZ-UHFFFAOYSA-N 3-anilinopropanoic acid Chemical compound OC(=O)CCNC1=CC=CC=C1 AQKKRXMVSOXABZ-UHFFFAOYSA-N 0.000 description 1
- GTTFYSJDNZFRLZ-UHFFFAOYSA-N 4-methyl-3,4-dihydro-1h-quinolin-2-one Chemical compound C1=CC=C2C(C)CC(=O)NC2=C1 GTTFYSJDNZFRLZ-UHFFFAOYSA-N 0.000 description 1
- TWYVITBRDNFBNT-UHFFFAOYSA-N 7-chloro-2-methyl-1h-quinolin-4-one Chemical compound C1=C(Cl)C=C2NC(C)=CC(=O)C2=C1 TWYVITBRDNFBNT-UHFFFAOYSA-N 0.000 description 1
- NAUSASURMPPZKZ-UHFFFAOYSA-N 7-chloro-2-methyl-2,3-dihydro-1h-quinolin-4-one Chemical compound C1=C(Cl)C=C2NC(C)CC(=O)C2=C1 NAUSASURMPPZKZ-UHFFFAOYSA-N 0.000 description 1
- JPVTWKDGBWUNBQ-UHFFFAOYSA-N 7-methyl-1h-quinolin-4-one Chemical compound OC1=CC=NC2=CC(C)=CC=C21 JPVTWKDGBWUNBQ-UHFFFAOYSA-N 0.000 description 1
- OVCDSSHSILBFBN-UHFFFAOYSA-N Amodiaquine Chemical compound C1=C(O)C(CN(CC)CC)=CC(NC=2C3=CC=C(Cl)C=C3N=CC=2)=C1 OVCDSSHSILBFBN-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- APQPGQGAWABJLN-UHFFFAOYSA-N Floctafenine Chemical compound OCC(O)COC(=O)C1=CC=CC=C1NC1=CC=NC2=C(C(F)(F)F)C=CC=C12 APQPGQGAWABJLN-UHFFFAOYSA-N 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 241001122767 Theaceae Species 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229940035676 analgesics Drugs 0.000 description 1
- 239000012491 analyte Substances 0.000 description 1
- 239000000730 antalgic agent Substances 0.000 description 1
- 230000000078 anti-malarial effect Effects 0.000 description 1
- 229940111121 antirheumatic drug quinolines Drugs 0.000 description 1
- 238000005899 aromatization reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 229960003677 chloroquine Drugs 0.000 description 1
- WHTVZRBIWZFKQO-UHFFFAOYSA-N chloroquine Natural products ClC1=CC=C2C(NC(C)CCCN(CC)CC)=CC=NC2=C1 WHTVZRBIWZFKQO-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 238000005695 dehalogenation reaction Methods 0.000 description 1
- 238000006356 dehydrogenation reaction Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 229960003240 floctafenine Drugs 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/20—Oxygen atoms
- C07D215/22—Oxygen atoms attached in position 2 or 4
- C07D215/233—Oxygen atoms attached in position 2 or 4 only one oxygen atom which is attached in position 4
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Quinoline Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8210615A FR2528836A1 (fr) | 1982-06-17 | 1982-06-17 | Procede de preparation d'hydroxy-4 quinoleines |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| HU189698B true HU189698B (en) | 1986-07-28 |
Family
ID=9275118
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| HU832157A HU189698B (en) | 1982-06-17 | 1983-06-16 | Process for preparing 4-hydroxy-quinolines from quinolinones |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4508902A (en16) |
| EP (1) | EP0097585B1 (en16) |
| JP (1) | JPS597170A (en16) |
| KR (1) | KR900006098B1 (en16) |
| AT (1) | ATE18762T1 (en16) |
| CA (1) | CA1193262A (en16) |
| DE (1) | DE3362676D1 (en16) |
| DK (1) | DK157018C (en16) |
| FR (1) | FR2528836A1 (en16) |
| HU (1) | HU189698B (en16) |
| IE (1) | IE55430B1 (en16) |
| IN (1) | IN159883B (en16) |
| ZA (1) | ZA834437B (en16) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01250380A (ja) * | 1987-12-26 | 1989-10-05 | Tokyo Tanabe Co Ltd | 光学活性ベンゾキノリジン誘導体、その製造方法およびそれを有効成分とする抗菌剤 |
| CN108794396B (zh) * | 2018-07-06 | 2020-06-02 | 浙江工业大学 | 4-氧代-2,3-二氢喹啉类化合物的氧化方法 |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2558211A (en) * | 1949-04-14 | 1951-06-26 | Lilly Co Eli | Preparation of 4-hydroxyquinoline compounds |
| FR2498186A1 (fr) * | 1981-01-16 | 1982-07-23 | Rhone Poulenc Sante | Preparation de la chloro-5, -6, -7 ou -8 hydroxy-4 quinoleine |
-
1982
- 1982-06-17 FR FR8210615A patent/FR2528836A1/fr active Granted
-
1983
- 1983-06-16 ZA ZA834437A patent/ZA834437B/xx unknown
- 1983-06-16 DE DE8383401242T patent/DE3362676D1/de not_active Expired
- 1983-06-16 AT AT83401242T patent/ATE18762T1/de not_active IP Right Cessation
- 1983-06-16 US US06/504,954 patent/US4508902A/en not_active Expired - Fee Related
- 1983-06-16 IN IN410/DEL/83A patent/IN159883B/en unknown
- 1983-06-16 KR KR8302692A patent/KR900006098B1/ko not_active Expired
- 1983-06-16 HU HU832157A patent/HU189698B/hu not_active IP Right Cessation
- 1983-06-16 CA CA000430583A patent/CA1193262A/fr not_active Expired
- 1983-06-16 JP JP58106816A patent/JPS597170A/ja active Granted
- 1983-06-16 IE IE1422/83A patent/IE55430B1/en unknown
- 1983-06-16 DK DK277783A patent/DK157018C/da not_active IP Right Cessation
- 1983-06-16 EP EP83401242A patent/EP0097585B1/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| KR840005102A (ko) | 1984-11-03 |
| DK157018B (da) | 1989-10-30 |
| EP0097585B1 (fr) | 1986-03-26 |
| DE3362676D1 (en) | 1986-04-30 |
| JPH0368861B2 (en16) | 1991-10-30 |
| DK277783A (da) | 1983-12-18 |
| ATE18762T1 (de) | 1986-04-15 |
| KR900006098B1 (en) | 1990-08-22 |
| DK157018C (da) | 1990-03-26 |
| JPS597170A (ja) | 1984-01-14 |
| FR2528836B1 (en16) | 1984-12-21 |
| IE831422L (en) | 1983-12-17 |
| US4508902A (en) | 1985-04-02 |
| IN159883B (en16) | 1987-06-13 |
| CA1193262A (fr) | 1985-09-10 |
| DK277783D0 (da) | 1983-06-16 |
| FR2528836A1 (fr) | 1983-12-23 |
| IE55430B1 (en) | 1990-09-12 |
| EP0097585A1 (fr) | 1984-01-04 |
| ZA834437B (en) | 1984-03-28 |
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