Dimethylformamide dimethyl acetal → HCID 728912, compound

HRID 421636Notes

Reaction equation

HRID 421636 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].CO[CH:13](OC)[N:14]([CH3:16])[CH3:15]>C(Cl)(Cl)Cl>[CH3:13][N:14](/[CH:16]=[C:3]1\[C:2](=[O:10])[NH:1][C:9]2[C:4]\1=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH3:15]

Participants

4

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 321710Oxindole

Product 1

HCID 728912HCID 728912, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 1,3-dihydro-2H-indol-2-one 25.0 g, 189 mmol) in CHCl3 (150 mL) was added N,N-dimethylformamide dimethyl acetal (29.2 mL, 209 mmol) and the reaction was heated at 70° C. under an atmosphere of argon. After 4.5 h, the reaction was cooled to RT and was concentrated. The resulting solid was triturated with ether and filtered to give (3Z)-3-[(dimethylamino)methylene]-1,3-dihydro-2H-indol-2-one as a yellow solid (iii-a, 33.0 g, 93%). NH4OAc QC conditions. DAD Retention Time=1.19 min. M+H=189.

Workup

  1. temperaturethe reaction was cooled to RT
  2. concentrationwas concentrated
  3. customThe resulting solid was triturated with ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-3eb08db2ee9245c095ee37e34a757270
Source dataset
uspto-grants-2012_01
Patent number
US08101604B2

Reaction notes

Loading…