Water → HCID 23313854, compound

HRID 745615Notes

Reaction equation

HRID 745615 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:11]([OH:13])=[O:12])=[CH:5]2.C(N([CH2:19][CH3:20])CC)C.C1(C)C=CC=CC=1.[C:28](OC(=O)C)(=[O:30])[CH3:29].[OH2:35]>CN(C)C1C=CN=CC=1>[C:28]([N:7]1[C:8]2[C:4](=[CH:3][C:2]([O:1][C:19](=[O:35])[CH3:20])=[CH:10][CH:9]=2)[CH:5]=[C:6]1[C:11]([OH:13])=[O:12])(=[O:30])[CH3:29]

Participants

7

Reactant 5

HCID 962WaterHCID 1140TolueneHCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 889585-Hydroxyindole-2-carboxylic acid

Product 1

HCID 23313854HCID 23313854, compound

Reagents, catalysts & solvents 1

HCID 142844-(Dimethylamino)pyridineCatalyst

Procedure

The starting material is prepared as follows: To the mixture of 10 g of 5-hydroxyindole-2-carboxylic acid, 29 g of triethylamine, 0.5 g of 4-dimethylaminopyridine and 50 ml of toluene, 23 g of acetic anhydride are added while stirring at room temperature. After 3 hours 150 ml of water are added and the mixture is stirred vigorously for 1 hour. The layers are separated, the organic phase is extracted with 50 ml of saturated aqueous sodium bicarbonate and the combined aqueous solutions washed with 100 ml of diethyl ether. They are acidified to pH=1 with concentrated hydrochloric acid, the precipitate formed is collected, washed 5 times with 50 ml of water and dried, to give the 1-acetyl-5-acetoxyindole-2-carboxylic acid melting at 142°-145°.

Workup

  1. customThe starting material is prepared
  2. additionare added
  3. stirringthe mixture is stirred vigorously for 1 hour
  4. customThe layers are separated
  5. extractionthe organic phase is extracted with 50 ml of saturated aqueous sodium bicarbonate
  6. washthe combined aqueous solutions washed with 100 ml of diethyl ether
  7. customthe precipitate formed
  8. customis collected
  9. washwashed 5 times with 50 ml of water
  10. customdried

Sources & evidence

ORD record
ord-bf0b5c5dfe9f459a83d8b716f1a74908
Source dataset
uspto-grants-1986_07
Patent number
US04599357

Reaction notes

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