Acetic Acid → HCID 66558667, compound

HRID 1474469Notes

Reaction equation

HRID 1474469 reaction equation
[CH2:1]([N:3]([CH2:30][CH3:31])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:17]2[CH2:16][CH2:15][CH2:14]/[C:13](=[C:18]3/[C:19](=[O:28])[NH:20][C:21]4[C:26]/3=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)/[C:12]=2[NH:11][C:10]=1[CH3:29])=[O:8])[CH3:2].C(#N)C.[C:35]([OH:38])(=[O:37])[CH3:36]>ClCCl>[C:35]([OH:38])(=[O:37])[CH3:36].[CH2:30]([N:3]([CH2:1][CH3:2])[CH2:4][CH2:5][NH:6][C:7]([C:9]1[C:17]2[CH2:16][CH2:15][CH2:14]/[C:13](=[C:18]3/[C:19](=[O:28])[NH:20][C:21]4[C:26]/3=[CH:25][C:24]([F:27])=[CH:23][CH:22]=4)/[C:12]=2[NH:11][C:10]=1[CH3:29])=[O:8])[CH3:31]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 6342AcetonitrileHCID 569355771032265-57-8

Product 1

HCID 66558667HCID 66558667, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

4.25 g (10 mmol) (Z)—N-[2-(diethylamino)ethyl]-2-methyl-7-(1,2-dihydro-5-fluoro-2-oxo-3H-indol-3-ylidene)-4,5,6,7-tetrahydro-1H-indol-3-carboxamide was added to a mixture of 250 ml acetonitrile and 50 ml dichloromethane. The mixture was treated under ultrasonic sound to uniform dispersion. 0.72 g (12 mmol) acetic acid was added and the solution was heated to reflux with stirring under nitrogen atmosphere. After reaction for 1 h, the resulting mixture was filtered while being hot, and the filtrate was concentrated at reduced pressure to dryness, added to 30 ml anhydrous ethanol and treated under ultrasonic sound to uniform dispersion. Then the solution was filtered, and the filter cake was dried at 40° C. under vacuum, to give the title compound as yellow solid (3.64 g, 7.5 mmol, yield 75%).

Workup

  1. additionThe mixture was treated under ultrasonic sound to uniform dispersion
  2. temperaturethe solution was heated
  3. temperatureto reflux
  4. customAfter reaction for 1 h
  5. filtrationthe resulting mixture was filtered
  6. concentrationthe filtrate was concentrated at reduced pressure to dryness
  7. additionadded to 30 ml anhydrous ethanol
  8. additiontreated under ultrasonic sound to uniform dispersion
  9. filtrationThen the solution was filtered
  10. customthe filter cake was dried at 40° C. under vacuum

Sources & evidence

ORD record
ord-9a65cd35c6c74c0cb941d5511f747654
Source dataset
uspto-grants-2015_04
Patent number
US09018242B2

Reaction notes

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