Acetic Anhydride → N-(3,4-Dichlorobenzyl)-5-acetoxyindole-2-carboxylic acid

HRID 1582650Notes

Reaction equation

HRID 1582650 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:16]([OH:18])=[O:17].[C:23](OC(=O)C)(=[O:25])[CH3:24]>C(OCC)(=O)C.CN(C)C1C=CN=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][C:21]=1[Cl:22])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][C:23](=[O:25])[CH3:24])=[CH:12][CH:13]=2)[CH:8]=[C:7]1[C:16]([OH:18])=[O:17]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 9949615N-(3,4-Dichlorobenzyl)-5-hydroxyindole-2-carboxylic acid

Product 1

HCID 22718737N-(3,4-Dichlorobenzyl)-5-acetoxyindole-2-carboxylic acid

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of N-(3,4-Dichlorobenzyl)-5-hydroxyindole-2-carboxylic acid (10 g) in warm ethyl acetate (250 ml) was added 4-dimethylaminopyridine (100 mg) and acetic anhydride (5.0 ml) and the resulting mixture was stirred for 2 hours. The organics were washed with 1N HCl and dried. Hexane was added to cause crystallision of the product. The solid was filtered and washed with hexane to give the desired product. (5 g, 44%). 1H NMR (DMSO-d6) δ 2.25 (s, 3H), 5.85 (s, 2H), 6.9 (dd, 1H), 7.05 (dd, 1H), 7.3-7.6 (m, 5H); m/z 378, 380 (MH+).

Workup

  1. washThe organics were washed with 1N HCl
  2. customdried
  3. additionHexane was added
  4. customcrystallision of the product
  5. filtrationThe solid was filtered
  6. washwashed with hexane

Sources & evidence

ORD record
ord-8f74b749bf5d4e83a3d8fe9045f41b9c
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

Loading…