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

HRID 1582646Notes

Reaction equation

HRID 1582646 reaction equation
CN(C1C=CC=CN=1)C.[C:10]([O:13][C:14](=O)[CH3:15])(=[O:12])[CH3:11].[Cl:17][C:18]1[CH:19]=[C:20]([CH:35]=[CH:36][C:37]=1[Cl:38])[CH2:21][N:22]1[C:30]2[C:25](=[CH:26]C(O)=C[CH:29]=2)[CH:24]=[C:23]1[C:32]([OH:34])=[O:33].C(O)C>C(OCC)(=O)C>[Cl:17][C:18]1[CH:19]=[C:20]([CH:35]=[CH:36][C:37]=1[Cl:38])[CH2:21][N:22]1[C:30]2[C:25](=[CH:26][C:14]([O:13][C:10](=[O:12])[CH3:11])=[CH:15][CH:29]=2)[CH:24]=[C:23]1[C:32]([OH:34])=[O:33]

Participants

6

Reactant 4

HCID 702EthanolHCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 9949615N-(3,4-Dichlorobenzyl)-5-hydroxyindole-2-carboxylic acid

Product 1

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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Dimethylaminopyridine (100 mg) and acetic anhydride (1.12 ml) were added to a solution of N-(3,4-Dichlorobenzyl)-5-hydroxyindole-2-carboxylic acid in ethyl acetate (50 ml) and stirred at ambient temperature for 1 hour. Ethanol (10 ml) was added and the reaction was stirred for 30 min. Solvent partially evaporated and iso-hexane added to give a precipitate, which was filtered off and dried to give the product as a white solid (1.2 g). NMR: δ 2.25 (s, 3H), 5.85 (s, 2H), 6.9 (dd, 1H), 7.3-7.6 (m, 5H); m/z 376, 378 (M−H+)

Workup

  1. stirringthe reaction was stirred for 30 min
  2. customSolvent partially evaporated
  3. additioniso-hexane added
  4. customto give a precipitate, which
  5. filtrationwas filtered off
  6. customdried

Sources & evidence

ORD record
ord-28a23c19d0374e478cd9179f05cfe639
Source dataset
uspto-grants-2004_05
Patent number
US06737435B1

Reaction notes

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