Water → N,N-diethyl-2-[2-amino-3-(2-fluorophenoxy)phenyl]acetamide
Reaction equation
[Cl-].[NH4+].O.[CH2:4]([N:6]([CH2:27][CH3:28])[C:7](=[O:26])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C:10]=1[N+:23]([O-])=O)[CH3:5].C(OCC)(=O)C>C(O)C.[Fe]>[CH2:27]([N:6]([CH2:4][CH3:5])[C:7](=[O:26])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C:10]=1[NH2:23])[CH3:28]Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of iron powder (5 g.), ammonium chloride (0.5 g.), ethanol (40 ml.) and water (20 ml.) and a solution of N,N-diethyl-2-[2-nitro-3-(2-fluorophenoxy)phenyl]acetamide (5.1 g.) in ethanol (5 ml.) were treated in a similar manner to that of Example 1-(1) [extraction solvent: ethyl acetate] to give oily N,N-diethyl-2-[2-amino-3-(2-fluorophenoxy)phenyl]acetamide (4.6 g.). This substance was dissolved in a mixture of methanol and hydrochloric acid. The solution was evaporated and the residue was pulverized with ethyl acetate. The resultant product (4.15 g.). was recrystallized from a mixture of ethanol and ethyl acetate to give white needles of the captioned compound (2.95 g.). mp 159° to 160° C.
Sources & evidence
- ORD record
- ord-a97f13174de7437d93ba741fe276734f
- Source dataset
- uspto-grants-1984_09
- Patent number
- US04472433
Reaction notes
Loading…