2-Aminophenol → 2-chloro-N-(2-hydroxyphenyl)acetamide
Reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].C(N(CC)CC)C.[Cl:16][CH2:17][C:18](Cl)=[O:19]>C(OCC)(=O)C>[Cl:16][CH2:17][C:18]([NH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8])=[O:19]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a mixture of 8.90 g (81.5 mmol) of 2-aminophenol and 11.4 ml (81.5 mmol) of triethylamine in 250 ml of ethyl acetate cooled at 0° C. were added over several minutes 6.5 ml (81.5 mmol) of chloroacetyl chloride. The reaction mixture was stirred at 0° C. for 100 min and then washed with saline, aqueous sodium bicarbonate, and saline. The organic layers were dried over magnesium sulfate and concentrated. Dichloromethane was added to the residue and the resulted solid collected and dried to give the title compound, mp 133°-134°; NMR (CDCl3) 4.27, 6.93, 7.02, 7.17, 7.25, 7.80 and 8.53 δ.
Workup
- washwashed with saline, aqueous sodium bicarbonate, and saline
- dry with materialThe organic layers were dried over magnesium sulfate
- concentrationconcentrated
- additionDichloromethane was added to the residue
- customthe resulted solid collected
- customdried
Sources & evidence
- ORD record
- ord-29f43ca87d5b43b390ac70a51ff02f2e
- Source dataset
- uspto-grants-1997_09
- Patent number
- US05668282
Reaction notes
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