Acetic Anhydride → 3-Acetylamino-4-methoxyphenylacetone

HRID 2179891Notes

Reaction equation

HRID 2179891 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9].[C:14](OC(=O)C)(=[O:16])[CH3:15]>C(Cl)(Cl)Cl.CN(C1C=CN=CC=1)C>[C:14]([NH:1][C:2]1[CH:3]=[C:4]([CH2:10][C:11](=[O:13])[CH3:12])[CH:5]=[CH:6][C:7]=1[O:8][CH3:9])(=[O:16])[CH3:15]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 207479003-Amino-4-methoxyphenylacetone

Product 1

HCID 697335313-Acetylamino-4-methoxyphenylacetoneYield 97%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolvent

Procedure

To the mixture of compound 11 (0.25 g, 1.39 mmol) in chloroform (30 ml) was added acetic anhydride (1.2 ml) and catalytic amount of DMAP (10 mg) at 0° C. After stirring at such temperature for 3 hours, no more starting materials were detected on TLC. The reaction was quenched by adding ice water, extracted with CH2Cl2 twice. The organic layer was washed with brine, dried over Na2SO4. Removal of the solvent afforded the crude product. Purification of the crude product by using silica gel column gave 0.3 g (97%) of desired product 12. 1HNMR(CDCl3): 8.25 (d, J=1.2 Hz, 1H), 7.79 (br, 1H), 6.81 (m, 2H), 3.86 (s, 3H), 3.64 (s, 2H), 2.20 (s, 3H), 1.95 (s, 3H).

Workup

  1. customThe reaction was quenched
  2. additionby adding ice water
  3. extractionextracted with CH2Cl2 twice
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent
  7. customafforded the crude product
  8. customPurification of the crude product

Sources & evidence

ORD record
ord-0c78fd5c701b40c4853a3fce2a69ab5b
Source dataset
uspto-grants-2005_05
Patent number
US06887867B2

Reaction notes

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