Hydrochloric Acid → 2-[2-(4-Carboxymethyl-2-chlorophenoxy)-1-methylethyl]amino-1-(3-chlorophenyl)ethanol
Reaction equation
[OH-].[K+].C[O:4][C:5]([CH2:7][C:8]1[CH:28]=[CH:27][C:11]([O:12][CH2:13][CH:14]([NH:16][CH2:17][CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[OH:19])[CH3:15])=[C:10]([Cl:29])[CH:9]=1)=[O:6].Cl>O.CO>[C:5]([CH2:7][C:8]1[CH:28]=[CH:27][C:11]([O:12][CH2:13][CH:14]([NH:16][CH2:17][CH:18]([C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([Cl:26])[CH:21]=2)[OH:19])[CH3:15])=[C:10]([Cl:29])[CH:9]=1)([OH:6])=[O:4]Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
A solution of 6.0 g of potassium hydroxide in 10 ml of water was added to a solution of 2.3 g of 2-[2-(4-methoxycarbonylmethyl-2-chlorophenoxy)-1-methylethyl]amino-1-(3-chlorophenyl)ethanol (prepared as described in Example 22) in 90 ml of methanol, and the resulting mixture was allowed to stand overnight. At the end of this time, the reaction mixture was poured into ice-water and the pH of the mixture was adjusted to a value of 7 by the addition of 1N aqueous hydrochloric acid, after which it was irradiated with ultrasonic waves. The crystals which precipitated were collected by filtration and recrystallized from methanol, to give 0.97 g of the title compound as crystals, melting at 188°-192° C.
Workup
- customafter which it was irradiated with ultrasonic waves
- customThe crystals which precipitated
- filtrationwere collected by filtration
- customrecrystallized from methanol
Sources & evidence
- ORD record
- ord-42e8ed99c6cb4fcf81dd136ab0726fe1
- Source dataset
- uspto-grants-1996_11
- Patent number
- US05576340
Reaction notes
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