Ammonium formate → HCID 21714313, compound

HRID 650054Notes

Reaction equation

HRID 650054 reaction equation
C([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:23])=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>[C].[Pd].C(O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH3:23])=[C:13]2[C:17]=1[NH:16][C:15]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:14]2

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 21714273HCID 21714273, compound

Product 1

HCID 21714313HCID 21714313, compoundYield 6.5%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

A mixture of ethyl 7-benzyloxy-4-methyl-1H-indole-2-carboxylate (15.0 g, 485 mmol), ammonium formate (30.6 g, 485 mmol), 10% palladium-carbon (2.00 g) and ethanol (450 ml) was heated under reflux for 0.5 hour. The reaction mixture was cooled to room temperature, after which the insoluble material was filtered off and the filtrate was concentrated under reduced pressure. The resulting residue was crystallized from ethyl acetate/toluene to obtain ethyl 7-hydroxy-4-methyl-1H-indole-2-carboxylate (6.96 g). M.p. 211-212° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 0.5 hour
  3. filtrationafter which the insoluble material was filtered off
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe resulting residue was crystallized from ethyl acetate/toluene

Sources & evidence

ORD record
ord-93150f6041bb46e6a6faff461f3bc8ba
Source dataset
uspto-grants-2001_08
Patent number
US06271251B1

Reaction notes

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