HCID 64088099, compound → HCID 63253034, compound

HRID 1467994Notes

Reaction equation

HRID 1467994 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11](=[O:15])[CH:12]([CH3:14])[CH3:13])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1>C(O)(=O)C.[Na]>[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([NH:10][C:11](=[O:15])[CH:12]([CH3:13])[CH3:14])=[CH:7][CH:8]=2)[CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 64088099HCID 64088099, compound

Product 1

HCID 63253034HCID 63253034, compoundYield 28.5%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 5360545SodiumSolvent

Procedure

To a stirred solution of N-(1H-indol-5-yl)isobutyramide (0.42 g, 2.9 mmol) in acetic acid (10 mL), sodium cynoborohydride (0.29 g, 4.6 mmol) was added at 0° C., and the reaction mixture was stirred at room temperature for 2-3 h. The reaction was quenched with water and neutralized by 50% NaOH solution, extracted with diethyl ether. The organic layer was separated and concentrated in vacuo to give N-(indolin-5-yl)isobutyramide (0.122 g, 28.5%); MS: 205.1 (M+1).

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with diethyl ether
  3. customThe organic layer was separated
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a85b6c8291c042e1b8ee142540e98cad
Source dataset
uspto-grants-2015_04
Patent number
US09000175B2

Reaction notes

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