KR870001147A - 2-아실-3,4-디알콕시 아닐린의 제조방법 - Google Patents
2-아실-3,4-디알콕시 아닐린의 제조방법 Download PDFInfo
- Publication number
- KR870001147A KR870001147A KR1019860006044A KR860006044A KR870001147A KR 870001147 A KR870001147 A KR 870001147A KR 1019860006044 A KR1019860006044 A KR 1019860006044A KR 860006044 A KR860006044 A KR 860006044A KR 870001147 A KR870001147 A KR 870001147A
- Authority
- KR
- South Korea
- Prior art keywords
- formula
- compound
- anilide
- acid
- reacted
- Prior art date
Links
- 238000000034 method Methods 0.000 title claims 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 title claims 3
- 150000003931 anilides Chemical class 0.000 claims 6
- 150000001875 compounds Chemical class 0.000 claims 5
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical group CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims 3
- 239000002253 acid Substances 0.000 claims 3
- 125000000217 alkyl group Chemical group 0.000 claims 3
- -1 pivalic acid compound Chemical class 0.000 claims 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 150000008065 acid anhydrides Chemical class 0.000 claims 2
- 125000001246 bromo group Chemical group Br* 0.000 claims 2
- 239000003153 chemical reaction reagent Substances 0.000 claims 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims 2
- 150000002900 organolithium compounds Chemical class 0.000 claims 2
- 125000002524 organometallic group Chemical group 0.000 claims 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims 1
- JVSFQJZRHXAUGT-UHFFFAOYSA-N 2,2-dimethylpropanoyl chloride Chemical compound CC(C)(C)C(Cl)=O JVSFQJZRHXAUGT-UHFFFAOYSA-N 0.000 claims 1
- ONIKNECPXCLUHT-UHFFFAOYSA-N 2-chlorobenzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1Cl ONIKNECPXCLUHT-UHFFFAOYSA-N 0.000 claims 1
- WICRYVIFEXZTME-UHFFFAOYSA-N 2-tert-butyl-5,6-dimethoxy-1,3-benzoxazin-4-one Chemical compound O1C(C(C)(C)C)=NC(=O)C2=C(OC)C(OC)=CC=C21 WICRYVIFEXZTME-UHFFFAOYSA-N 0.000 claims 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 claims 1
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims 1
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 125000001153 fluoro group Chemical group F* 0.000 claims 1
- 150000004820 halides Chemical class 0.000 claims 1
- 230000007062 hydrolysis Effects 0.000 claims 1
- 238000006460 hydrolysis reaction Methods 0.000 claims 1
- 229910052744 lithium Inorganic materials 0.000 claims 1
- NXPHGHWWQRMDIA-UHFFFAOYSA-M magnesium;carbanide;bromide Chemical group [CH3-].[Mg+2].[Br-] NXPHGHWWQRMDIA-UHFFFAOYSA-M 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- IJMZVJYAZOWEOK-UHFFFAOYSA-N n-(2-acetyl-3,4-dimethoxyphenyl)-2,2-dimethylpropanamide Chemical compound COC1=CC=C(NC(=O)C(C)(C)C)C(C(C)=O)=C1OC IJMZVJYAZOWEOK-UHFFFAOYSA-N 0.000 claims 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C225/00—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones
- C07C225/22—Compounds containing amino groups and doubly—bound oxygen atoms bound to the same carbon skeleton, at least one of the doubly—bound oxygen atoms not being part of a —CHO group, e.g. amino ketones having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/04—1,3-Oxazines; Hydrogenated 1,3-oxazines
- C07D265/12—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems
- C07D265/14—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring
- C07D265/20—1,3-Oxazines; Hydrogenated 1,3-oxazines condensed with carbocyclic rings or ring systems condensed with one six-membered ring with hetero atoms directly attached in position 4
- C07D265/22—Oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Luminescent Compositions (AREA)
- Steroid Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Abstract
내용 없음.
Description
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음
Claims (10)
- 일반식(1)의 치환된 아닐린을 일반식(7)의 피발산 화합물과 반응시켜 일반식(2)의 아닐리드를 생성시키고, 생성된 아닐리드를 우선 일반식(8)의 유기리튬 화합물과 반응시켜 수득한 생성물을 이산화탄소와 반응시켜 일반식(3)의 아닐리드를 생성시킨 후, 생성된 아닐리드를 일반식(9)의 산 무수물과 반응시켜 일반식(4)의 1,3-벤즈옥사진-4온을 생성시키고, 이 1,3-벤즈옥사진-4온을 일반식(10)의 유기금속시약과 반응시켜 일반식(5)의 아닐리드를 생성시킨 다음, 생성된 일반식(5)의 아닐리드를 산으로 가수분해시킴을 특징으로 하여 일반식(6)의 화합물을 제조하는 방법.상기 식에서,R1,R2,R3및 R5는 각각 저급알킬이고, R2및 R3가 함께는 메틸렌 디옥시그룹이며, R4는 클로로, 브로모,플루오로 또는 OCOC(CH3)3이고, R은 n-부틸, 2급-부틸, 또는 3급-부틸이며, M은 리튬 또는 MgX(여기서, X는 클로로 또는 브로모이다)이다.
- 제1항에 있어서, 일반식(7)의 산 할라이드가 피발로일 클로라이드인 방법.
- 제1항에 있어서, 유기리튬 화합물이 n-부틸리튬인 방법.
- 제1항에 있어서, 산 무수물이 아세트산 무수물인 방법.
- 제1항에 있어서, 유기금속 시약이 메틸마그네슘 브로마이드인 방법.
- 제1항에 있어서, 산이 황산인 방법.
- 하기 일반식의 화합물.여기서, R2및 R3는 저급 알킬이다.
- 제7항에 있어서, 3급-부틸-5,6-디메톡시-1,3-벤즈옥사진-4-온인 화합물.
- 하기 일반식의 화합물.여기서, R2및 R3는 저급 알킬이다.
- 제9항에 있어서, 2′-아세틸-3′,4′-디메톡시-2,2-디메틸-프로피오아닐리드인 화합물.※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US760003 | 1985-07-29 | ||
US06/760,003 US4731480A (en) | 1985-07-29 | 1985-07-29 | Process for preparing 2-acyl-3,4-dialkoxyanilines |
Publications (2)
Publication Number | Publication Date |
---|---|
KR870001147A true KR870001147A (ko) | 1987-03-11 |
KR900003787B1 KR900003787B1 (ko) | 1990-05-31 |
Family
ID=25057746
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
KR1019860006044A KR900003787B1 (ko) | 1985-07-29 | 1986-07-24 | 2-아실-3,4-디알콕시아닐린의 제조방법 |
Country Status (17)
Country | Link |
---|---|
US (1) | US4731480A (ko) |
EP (1) | EP0211588B1 (ko) |
JP (1) | JPS6253948A (ko) |
KR (1) | KR900003787B1 (ko) |
AT (1) | ATE50560T1 (ko) |
AU (1) | AU585378B2 (ko) |
CA (1) | CA1269979A (ko) |
DE (1) | DE3669151D1 (ko) |
DK (1) | DK358586A (ko) |
ES (1) | ES2001043A6 (ko) |
FI (1) | FI863083A (ko) |
GR (1) | GR861975B (ko) |
HK (1) | HK77290A (ko) |
HU (1) | HUT44759A (ko) |
NO (1) | NO863046L (ko) |
SG (1) | SG61090G (ko) |
ZA (1) | ZA865623B (ko) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4571405A (en) * | 1984-05-29 | 1986-02-18 | Miles Laboratories, Inc. | Anti-allergic chromone- or thiochromone-5-oxamic acid derivatives, compositions, and method of use therefor |
US4883787A (en) * | 1985-07-29 | 1989-11-28 | Ortho Pharmaceutical Corporation | Process for preparing 2-acyl-3, 4-dialkoxyanilines |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH194648A (de) * | 1934-11-20 | 1937-12-15 | Ig Farbenindustrie Ag | Verfahren zur Darstellung eines 4,5-alkylsubstituierten 2-Aminodiarylketons. |
NL241184A (ko) * | 1958-07-12 | |||
US3405126A (en) * | 1965-01-11 | 1968-10-08 | Daiichi Seiyaku Co | 4-hydroxy-7-amino-3-sulfanylamide-coumarin |
GR32433B (el) * | 1966-02-05 | 1967-07-04 | Societe D' Etudes Scientifiques Et Industrielles De L' Ile - D... | Μεθοδος παρασκευης παραγωγων του 5 - αλογονοσαλικυλικου οξεως |
BG16442A3 (bg) * | 1967-10-30 | 1972-11-20 | Max Denzer | Метод за получаване на нови о-изопропиламинобензофенони |
US3634455A (en) * | 1969-05-28 | 1972-01-11 | Upjohn Co | 2 3-disubstituted 3h-indol-3-ols and a process of production therefor |
EP0010348A1 (en) * | 1978-09-12 | 1980-04-30 | Imperial Chemical Industries Plc | Heterocyclic trichloromethyl derivatives, process for their preparation and their use |
DE2934543A1 (de) * | 1979-08-27 | 1981-04-02 | Basf Ag, 6700 Ludwigshafen | Substituierte n-benzoylanthranilsaeurederivate und deren anydroverbindungen, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
FR2482596A1 (fr) * | 1980-05-19 | 1981-11-20 | Roussel Uclaf | Nouveaux derives de l'acide 4-hydroxy 3-quinoleine carboxylique substitues en 2, leur procede de preparation et leur application comme medicament |
US4453004A (en) * | 1982-04-01 | 1984-06-05 | International Telephone And Telegraph Corporation | Process for the alkylation of phenolic compounds |
US4453018A (en) * | 1982-04-01 | 1984-06-05 | International Telephone And Telegraph Corporation | Process for the alkylation of phenolic compounds with alkyl sulfites |
US4490374A (en) | 1982-09-30 | 1984-12-25 | Ortho Pharmaceutical Corporation | 5,6-Dialkoxy-3,4-optionally substituted-2(1H)quinazolinones, composition and method of use |
US4555571A (en) * | 1983-09-29 | 1985-11-26 | Ortho Pharmaceutical Corporation | Substituted 2(1H)-quinazolinone-1-alkanoic acids and esters |
US4556739A (en) * | 1983-09-29 | 1985-12-03 | Ortho Pharmaceutical Corporation | 3,4-Dialkoxy-2-alkylcarbonyl analino compounds |
-
1985
- 1985-07-29 US US06/760,003 patent/US4731480A/en not_active Expired - Lifetime
-
1986
- 1986-07-24 KR KR1019860006044A patent/KR900003787B1/ko active IP Right Grant
- 1986-07-28 GR GR861975A patent/GR861975B/el unknown
- 1986-07-28 AU AU60631/86A patent/AU585378B2/en not_active Ceased
- 1986-07-28 JP JP61175808A patent/JPS6253948A/ja active Pending
- 1986-07-28 FI FI863083A patent/FI863083A/fi not_active IP Right Cessation
- 1986-07-28 ES ES8600655A patent/ES2001043A6/es not_active Expired
- 1986-07-28 DK DK358586A patent/DK358586A/da not_active Application Discontinuation
- 1986-07-28 EP EP86305767A patent/EP0211588B1/en not_active Expired - Lifetime
- 1986-07-28 HU HU863214A patent/HUT44759A/hu unknown
- 1986-07-28 DE DE8686305767T patent/DE3669151D1/de not_active Expired - Lifetime
- 1986-07-28 AT AT86305767T patent/ATE50560T1/de not_active IP Right Cessation
- 1986-07-28 NO NO863046A patent/NO863046L/no unknown
- 1986-07-28 ZA ZA865623A patent/ZA865623B/xx unknown
- 1986-07-29 CA CA000514892A patent/CA1269979A/en not_active Expired - Lifetime
-
1990
- 1990-07-21 SG SG610/90A patent/SG61090G/en unknown
- 1990-09-27 HK HK772/90A patent/HK77290A/xx unknown
Also Published As
Publication number | Publication date |
---|---|
US4731480A (en) | 1988-03-15 |
DE3669151D1 (de) | 1990-04-05 |
AU6063186A (en) | 1987-02-05 |
AU585378B2 (en) | 1989-06-15 |
DK358586D0 (da) | 1986-07-28 |
DK358586A (da) | 1987-01-30 |
FI863083A0 (fi) | 1986-07-28 |
NO863046D0 (no) | 1986-07-28 |
HUT44759A (en) | 1988-04-28 |
ATE50560T1 (de) | 1990-03-15 |
CA1269979A (en) | 1990-06-05 |
SG61090G (en) | 1990-09-07 |
KR900003787B1 (ko) | 1990-05-31 |
ES2001043A6 (es) | 1988-04-16 |
ZA865623B (en) | 1988-03-30 |
EP0211588B1 (en) | 1990-02-28 |
GR861975B (en) | 1986-12-22 |
JPS6253948A (ja) | 1987-03-09 |
EP0211588A1 (en) | 1987-02-25 |
NO863046L (no) | 1987-01-30 |
HK77290A (en) | 1990-10-05 |
FI863083A (fi) | 1987-01-30 |
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