Acetic Anhydride → N-(2-Oxoindolin-6-yl)acetamide

HRID 1615200Notes

Reaction equation

HRID 1615200 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]2[C:5]([CH2:6][C:7](=[O:11])[NH:8]2)=[CH:4][CH:3]=1.[C:12](OC(=O)C)(=[O:14])[CH3:13]>C1COCC1>[O:11]=[C:7]1[CH2:6][C:5]2[C:9](=[CH:10][C:2]([NH:1][C:12](=[O:14])[CH3:13])=[CH:3][CH:4]=2)[NH:8]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 5905386-Amino-1,3-dihydro-2H-indol-2-one

Product 1

HCID 2749839N-(2-Oxoindolin-6-yl)acetamideYield 66%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 6-aminoindolin-2-one (30 mg, 0.202 mmol) in THF (1 mL) was added acetic anhydride (19 uL, 0.202 mmol). After 2 hrs the product was precipitated with ether, filtered and dried to give 25 mg, 66% of a white solid. 1H NMR (400 MHz, CD3OD) δ 7.41 (s, 1H), 7.16 (d, J=7.0 Hz, 1H), 7.00 (d, J=8.0 Hz, 1H), 3.49 (s, 2H), 2.12 (s, 3H); MS ESI 191.0 [M+H]+, calcd for [C10H10N2O2+H]+ 191.08.

Workup

  1. customAfter 2 hrs the product was precipitated with ether
  2. filtrationfiltered
  3. customdried

Sources & evidence

ORD record
ord-744eb831cee541408baeb63f8b998593
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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