1,2-Dichloroethane → HCID 86651952, compound

HRID 1615256Notes

Reaction equation

HRID 1615256 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[NH:9][C:8](=[O:11])[CH2:7]2.C(Cl)CCl.[CH:16](O)=[O:17]>C(Cl)Cl>[O:11]=[C:8]1[CH2:7][C:6]2[C:10](=[C:2]([NH:1][CH:16]=[O:17])[CH:3]=[CH:4][CH:5]=2)[NH:9]1

Participants

5

Reactant 3

HCID 111,2-DichloroethaneHCID 284Formic AcidHCID 64233127-aminoindolin-2-one

Product 1

HCID 86651952HCID 86651952, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 7-aminooxindole (32 mg, 0.22 mmol) in CH2Cl2 (1 mL) was added EDC (83 mg, 0.43 mmol) and formic acid (12 mg, 0.26 mmol). The reaction mixture was stirred at rt for 2 h and then filtered. The filter cake was washed with diethyl ether to give the title compound as a grey solid (27 mg, 71%). 1H NMR (400 MHz, CD3OD) δ 8.23 (s, 1H), 7.20 (d, 1H, J=8 Hz), 7.15 (d, 1H, J=8 Hz), 7.02 (t, 1H, J=8 Hz), 3.59 (s, 2H); MS ESI [M+H]+, calcd for [C9H8N2O2+H]+ 177.07. found m/z 177.0.

Workup

  1. filtrationfiltered
  2. washThe filter cake was washed with diethyl ether

Sources & evidence

ORD record
ord-95ad5c08665d4b2dbc9e4ebca9c1ea32
Source dataset
uspto-grants-2014_07
Patent number
US08765748B2

Reaction notes

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