1-Hydroxybenzotriazole → 6-Hydroxynaphthalene-2-carboxamide

HRID 1295902ノート

反応式

HRID 1295902 の反応式
[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

参加物

7

反応物 4

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

生成物 2

HCID 222AmmoniaHCID 143234946-Hydroxynaphthalene-2-carboxamide収率 58.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-c390dd88447e4ca09e71ae43532edd44
出典データセット
uspto-grants-2007_07
特許番号
US07244766B2

反応ノート

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