DE631855C - Verfahren zur Darstellung von N-(Aminoalkyl)-anthranilsaeurealkylestern - Google Patents
Verfahren zur Darstellung von N-(Aminoalkyl)-anthranilsaeurealkylesternInfo
- Publication number
- DE631855C DE631855C DEI50255D DEI0050255D DE631855C DE 631855 C DE631855 C DE 631855C DE I50255 D DEI50255 D DE I50255D DE I0050255 D DEI0050255 D DE I0050255D DE 631855 C DE631855 C DE 631855C
- Authority
- DE
- Germany
- Prior art keywords
- anthranilic acid
- aminoalkyl
- preparation
- alkyl esters
- parts
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 125000004103 aminoalkyl group Chemical group 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 5
- 238000002360 preparation method Methods 0.000 title claims description 3
- RWZYAGGXGHYGMB-UHFFFAOYSA-N o-aminobenzenecarboxylic acid Natural products NC1=CC=CC=C1C(O)=O RWZYAGGXGHYGMB-UHFFFAOYSA-N 0.000 claims description 12
- -1 aminoalkyl halide Chemical class 0.000 claims description 6
- 125000003277 amino group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical group Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000013078 crystal Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- SPEGUNZOHLFGCL-UHFFFAOYSA-N 2-(ethylamino)benzoic acid Chemical compound CCNC1=CC=CC=C1C(O)=O SPEGUNZOHLFGCL-UHFFFAOYSA-N 0.000 description 2
- YMDNODNLFSHHCV-UHFFFAOYSA-N 2-chloro-n,n-diethylethanamine Chemical compound CCN(CC)CCCl YMDNODNLFSHHCV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- TWLLPUMZVVGILS-UHFFFAOYSA-N Ethyl 2-aminobenzoate Chemical compound CCOC(=O)C1=CC=CC=C1N TWLLPUMZVVGILS-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- KJFMBFZCATUALV-UHFFFAOYSA-N phenolphthalein Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2C(=O)O1 KJFMBFZCATUALV-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- WNRWEBKEQARBKV-UHFFFAOYSA-N 1-(2-chloroethyl)piperidine Chemical compound ClCCN1CCCCC1 WNRWEBKEQARBKV-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- MCRWZBYTLVCCJJ-DKALBXGISA-N [(1s,3r)-3-[[(3s,4s)-3-methoxyoxan-4-yl]amino]-1-propan-2-ylcyclopentyl]-[(1s,4s)-5-[6-(trifluoromethyl)pyrimidin-4-yl]-2,5-diazabicyclo[2.2.1]heptan-2-yl]methanone Chemical compound C([C@]1(N(C[C@]2([H])C1)C(=O)[C@@]1(C[C@@H](CC1)N[C@@H]1[C@@H](COCC1)OC)C(C)C)[H])N2C1=CC(C(F)(F)F)=NC=N1 MCRWZBYTLVCCJJ-DKALBXGISA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 238000007281 aminoalkylation reaction Methods 0.000 description 1
- 230000003444 anaesthetic effect Effects 0.000 description 1
- 125000006309 butyl amino group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 229960003750 ethyl chloride Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000003589 local anesthetic agent Substances 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B61—RAILWAYS
- B61F—RAIL VEHICLE SUSPENSIONS, e.g. UNDERFRAMES, BOGIES OR ARRANGEMENTS OF WHEEL AXLES; RAIL VEHICLES FOR USE ON TRACKS OF DIFFERENT WIDTH; PREVENTING DERAILING OF RAIL VEHICLES; WHEEL GUARDS, OBSTRUCTION REMOVERS OR THE LIKE FOR RAIL VEHICLES
- B61F17/00—Lubrication specially adapted for axle-boxes of rail vehicles
- B61F17/02—Lubrication specially adapted for axle-boxes of rail vehicles with oil
- B61F17/14—Rotating lubricating devices
- B61F17/20—Rotating lubricating devices with scoops or the like attached to, or coupled with, the axle
Landscapes
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Engineering & Computer Science (AREA)
- Mechanical Engineering (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
- General Details Of Gearings (AREA)
Priority Applications (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| NL21797D NL21797C (enEXAMPLES) | 1934-07-26 | ||
| GB20223/28A GB320399A (en) | 1934-07-26 | 1928-07-11 | Improvements in or relating to axle boxes |
| FR657531D FR657531A (fr) | 1934-07-26 | 1928-07-16 | Boîte de palier à graissage automatique pour véhicules de voies ferrées |
| DEI50255D DE631855C (de) | 1934-07-26 | 1934-07-26 | Verfahren zur Darstellung von N-(Aminoalkyl)-anthranilsaeurealkylestern |
| GB21162/35A GB460249A (en) | 1934-07-26 | 1935-07-25 | Manufacture of n-(aminoalkyl)-anthranilic acid alkyl esters |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEI50255D DE631855C (de) | 1934-07-26 | 1934-07-26 | Verfahren zur Darstellung von N-(Aminoalkyl)-anthranilsaeurealkylestern |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE631855C true DE631855C (de) | 1936-06-29 |
Family
ID=6539699
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEI50255D Expired DE631855C (de) | 1934-07-26 | 1934-07-26 | Verfahren zur Darstellung von N-(Aminoalkyl)-anthranilsaeurealkylestern |
Country Status (4)
| Country | Link |
|---|---|
| DE (1) | DE631855C (enEXAMPLES) |
| FR (1) | FR657531A (enEXAMPLES) |
| GB (2) | GB320399A (enEXAMPLES) |
| NL (1) | NL21797C (enEXAMPLES) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3870715A (en) * | 1972-03-09 | 1975-03-11 | Nikolaus R Hansl | Substituted amino ethyl meta benzoic acid esters |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1153050B (de) * | 1958-07-08 | 1963-08-22 | Isothermos Sa Soc Gen | Achslagerkasten, insbesondere fuer Kippwagen |
-
0
- NL NL21797D patent/NL21797C/xx active
-
1928
- 1928-07-11 GB GB20223/28A patent/GB320399A/en not_active Expired
- 1928-07-16 FR FR657531D patent/FR657531A/fr not_active Expired
-
1934
- 1934-07-26 DE DEI50255D patent/DE631855C/de not_active Expired
-
1935
- 1935-07-25 GB GB21162/35A patent/GB460249A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3870715A (en) * | 1972-03-09 | 1975-03-11 | Nikolaus R Hansl | Substituted amino ethyl meta benzoic acid esters |
Also Published As
| Publication number | Publication date |
|---|---|
| GB460249A (en) | 1937-01-25 |
| NL21797C (enEXAMPLES) | |
| GB320399A (en) | 1929-10-11 |
| FR657531A (fr) | 1929-06-04 |
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