Acetic Acid → HCID 54128456, compound

HRID 1600646Notes

Reaction equation

HRID 1600646 reaction equation
C([O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[C:14]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:15]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:11]([Cl:32])[CH:10]=1)C1C=CC=CC=1.Cl.C(O)(=O)C>[C].[Pd].CN(C)C=O>[Cl:32][C:11]1[CH:10]=[C:9]([OH:8])[CH:17]=[C:16]2[C:12]=1[CH:13]=[C:14]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[N:15]2[CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]

Participants

6

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 54148313HCID 54148313, compound

Product 1

HCID 54128456HCID 54128456, compoundYield 54.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 6-benzyloxy-4-chloro-1-(4-ethoxycarbonylbutyl)-1H-indolecarboxylate (15.0 g, 32.8 mmol), 35% hydrochloric acid (3.3 ml), acetic acid (240 ml), 10% palladium-carbon (1.5 g) and N,N-dimethylformamide (60 ml) was stirred under a hydrogen atmosphere at room temperature for about 1 hour. The catalyst was filtered off and the filtrate was poured into a cooled 5% aqueous sodium chloride solution and extracted twice with ethyl acetate. The extract solution was washed three times with a 5% aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was crystallized from toluene to obtain 6.57 g of ethyl 4-chloro-1-(4-ethoxycarbonylbutyl)-6-hydroxy-1H-indolecarboxylate.

Workup

  1. filtrationThe catalyst was filtered off
  2. additionthe filtrate was poured into a cooled 5% aqueous sodium chloride solution
  3. extractionextracted twice with ethyl acetate
  4. washThe extract solution was washed three times with a 5% aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe resulting residue was crystallized from toluene

Sources & evidence

ORD record
ord-d5109d24848f43faa01f12c0bb113ce3
Source dataset
uspto-grants-1999_11
Patent number
US05977100

Reaction notes

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