Acetyl chloride → HCID 44359309, compound

HRID 551778Notes

Reaction equation

HRID 551778 reaction equation
Cl.[NH2:2][CH2:3][CH:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[CH:9]=[CH:8][CH:7]=1)[OH:5].C(=O)([O-])[O-].[K+].[K+].[C:24](Cl)(=[O:26])[CH3:25]>O.C(OCC)(=O)C>[OH:5][CH:4]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([O:16][CH3:17])[CH:14]=2)[CH:9]=[CH:8][CH:7]=1)[CH2:3][NH:2][C:24](=[O:26])[CH3:25]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 11430Potassium CarbonateHCID 445416702-Amino-1-(7-methoxy-1-naphthyl)ethanol hydrochloride

Product 1

HCID 44359309HCID 44359309, compound

Reagents, catalysts & solvents 1

HCID 22728543Water ethylacetateSolvent

Conditions

Temperature
0 °C

Procedure

The compound obtained in Step E (20 mmol) is dissolved in a mixture of water/ethyl acetate (25 ml/75 ml) cooled to 0° C. Potassium carbonate (60 mmol) is added, and then acetyl chloride (26 mmol) is added dropwise to the reaction mixture. The mixture is stirred vigorously for 30 minutes at ambient temperature. The two phases are separated and the organic phase is washed with 0.1M aqueous hydrochloric acid solution and then with water. After drying over magnesium sulphate, the organic phase is evaporated under reduced pressure. The residue obtained is recrystallised from acetonitrile to yield the title product in the form of a white solid.

Workup

  1. customThe two phases are separated
  2. washthe organic phase is washed with 0.1M aqueous hydrochloric acid solution
  3. dry with materialAfter drying over magnesium sulphate
  4. customthe organic phase is evaporated under reduced pressure
  5. customThe residue obtained
  6. customis recrystallised from acetonitrile

Sources & evidence

ORD record
ord-f2bc9330ad344068a5eecf2f38f2ba1d
Source dataset
uspto-grants-2011_05
Patent number
US07947852B2

Reaction notes

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