Acetic Anhydride → HCID 18941450, compound

HRID 356220Notes

Reaction equation

HRID 356220 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[NH2:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]2([CH3:26])[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:25])[CH:12]=[CH:13][CH:14]=1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[C:1]([NH:8][C:9]1[CH:10]=[C:11]([CH2:15][C:16]2([CH3:26])[CH2:24][C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17]2=[O:25])[CH:12]=[CH:13][CH:14]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 516892Sodium BicarbonateHCID 18941413HCID 18941413, compound

Product 1

HCID 18941450HCID 18941450, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

Acetic anhydride (41.75 mL, 0.46 mol) was added to a stirred solution of 2-[(3-aminophenyl)methyl]-2-methyl-1-indanone (37.00 g, 0.147 mol) in ethyl acetate (800 mL) and this mixture was stirred at room temperature for 2 h. Saturated sodium bicarbonate (600 mL) was added to the resulting mixture, followed by successive washes of the aqueous layer with ethyl acetate. The combined organic extracts were washed with water (500 mL), dried (MgSO4) and concentrated in vacuo to give the title compound as an oil: 1H NMR (CDCl3) 7.7 (doublet, 1H), 7.55-7.15 (multiplet, 5H), 7.1 (doublet, 1H), 6.85 (doublet, 1H), 3.25 (doublet, 1H), 2.9 (doublet, 1H), 2.7 (doublet, 1H), 2.1 (singlet, 3H), 2.1 (doublet, 1H), 1.2 (singlet, 3H).

Workup

  1. washThe combined organic extracts were washed with water (500 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4f0144f8f0b74b1b92ea6724c6098633
Source dataset
uspto-grants-1998_11
Patent number
US05834521

Reaction notes

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