Hydrochloric Acid → HCID 19101761, compound

HRID 1974562Notes

Reaction equation

HRID 1974562 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2.[H-].[Na+].[N+:19]([C:22]1[CH:23]=[C:24]([CH:34]=[CH:35][CH:36]=1)[C:25](OC1C=CC=CC=1)=[O:26])([O-:21])=[O:20].Cl>CN(C)C=O.O1CCCC1.C(OCC)(=O)C>[CH3:1][C:2]1[N:3]([C:25](=[O:26])[C:24]2[CH:34]=[CH:35][CH:36]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[C:4]2[C:9]([C:10]=1[CH2:11][CH2:12][CH2:13][C:14]([OH:16])=[O:15])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 922304phenyl 3-nitrobenzoateHCID 150472604-(2-Methyl-1H-indol-3-yl)butanoic acid

Product 1

HCID 19101761HCID 19101761, compoundYield 74.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolvent2×HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
20 °C

Procedure

A solution of 4-(2-methylindol-3-yl)butyric acid (600 mg) in N,N-dimethylformamide (10 ml) was added to a suspension of sodium hydride (60% dispersion in mineral oil, 243 mg) in N,N-dimethylformamide (5 ml) at 20° C. and the mixture was stirred at 20° C. for 1 hour. A solution of phenyl 3-nitrobenzoate (671 mg) in tetrahydrofuran (10 ml) was added to the mixture at -35° C. and the resulting mixture was stirred at the same temperature for 2 hours. The mixture was poured into a mixture of ethyl acetate and 1N hydrochloric acid. The organic layer was separated, washed with water and brine, and dried over magnesium sulfate. After evaporation of solvent, the residue was chromatographed on a silica gel (25 g) column with a mixture of hexane and ethyl acetate (10:1 to 1:1) to give 4-[2-methyl-1-(3-nitrobenzoyl)indol-3-yl]butyric acid (749 mg) as yellow crystals.

Workup

  1. stirringthe resulting mixture was stirred at the same temperature for 2 hours
  2. customThe organic layer was separated
  3. washwashed with water and brine
  4. dry with materialdried over magnesium sulfate
  5. customAfter evaporation of solvent
  6. customthe residue was chromatographed on a silica gel (25 g) column with a mixture of hexane and ethyl acetate (10:1 to 1:1)

Sources & evidence

ORD record
ord-9b1dcc5fc6154995992afce66483e737
Source dataset
uspto-grants-1994_02
Patent number
US05283251

Reaction notes

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