1-Hydroxybenzotriazole → 6-Hydroxynaphthalene-2-carboxamide

HRID 490845노트

반응식

HRID 490845 반응식
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([OH:14])=O)[CH:6]=[CH:5]2.Cl.C[N:17](C)CCCN=C=NCC.O[N:28]1C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[NH4+].[NH4+]>CN(C)C=O>[NH3:17].[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([NH2:28])=[O:14])[CH:6]=[CH:5]2

참가 물질

7

반응물 4

HCID 757711-HydroxybenzotriazoleHCID 855576-Hydroxy-2-naphthoic acidHCID 517111Ammonium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

생성물 2

HCID 222AmmoniaHCID 143234946-Hydroxynaphthalene-2-carboxamide수율 58.8%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

A solution of 6-hydroxy-2-napthoic acid (1.88 g, 9.99 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.11 g, 10.98 mmol), 1-hydroxybenzotriazole (1.48 g, 10.98 mmol) and ammonium carbonate (4.80 g, 49.95 mmol) in N,N-dimethylformamide (70 ml) was left to stir at room temperature under a nitrogen atmosphere for 3 days. The solvent was removed in vacuo and the residue partitioned between saturated aqueous sodium hydrogen carbonate (50 ml) and ethyl acetate (6 ×50 ml). The combined organic extracts were washed with water (25 ml), saturated aqueous sodium chloride (25 ml), dried (sodium sulfate) and the solvent removed in vacuo. The solid was absorbed onto silica gel and purified by column chromatography on silica gel eluting with dichloromethane:methanol:0.880 ammonia (95:5:0.5 changing to 90:10:1) to give the title compound as a pale yellow solid (1.1 g).

후처리

  1. customThe solvent was removed in vacuo
  2. customthe residue partitioned between saturated aqueous sodium hydrogen carbonate (50 ml) and ethyl acetate (6 ×50 ml)
  3. washThe combined organic extracts were washed with water (25 ml), saturated aqueous sodium chloride (25 ml)
  4. dry with materialdried (sodium sulfate)
  5. customthe solvent removed in vacuo
  6. customThe solid was absorbed onto silica gel
  7. custompurified by column chromatography on silica gel eluting with dichloromethane

출처 및 근거

ORD 기록
ord-56ee9b45cf7e47b69153ba015d097639
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528170B2

반응 노트

불러오는 중…