3-Chloro-4-methoxyaniline → HCID 69473762, compound
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][C:10](Cl)=O)[CH:6]=[CH:7][CH:8]=1.[Cl:13][C:14]1[CH:15]=[C:16]([NH2:22])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]>>[Cl:13][C:14]1[CH:15]=[C:16]([N:22]([CH2:10][CH2:9][C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=2)[C:3](=[O:2])[CH2:8][CH3:7])[CH:17]=[CH:18][C:19]=1[O:20][CH3:21]Participants
3
Procedure
According to synthetic methods F and G, N-(3-chloro-4-methoxy-phenyl)-N-[2-(3-methoxy-phenyl)-ethyl]-propionamide (0.753 g) was obtained from (3-methoxy-phenyl)-acetyl chloride (1.0 eq) and 3-chloro-4-methoxy-phenylamine (1.0 eq) followed by reaction with propionyl chloride (1.5 eq). MS: 348.4 (MH+); HPLC tR: 2.72 mm (method D); TLC Rf: 0.48 (ethyl acetate:hexane-1:1). According to synthetic methods H and B, the title compound (0.25 g) was obtained after purification by chromatography on silica gel (eluant: a gradient of 0 to 5% methanol in methylene chloride); MS: 304.2, 306.2 (MH+); HPLC tR: 1.80 min (method D); TLC Rf: 0.16 (2% methanol:methylene chloride).
Sources & evidence
- ORD record
- ord-4af9d53246b34a849cdbdce48a968723
- Source dataset
- uspto-grants-2007_08
- Patent number
- US07256201B2
Reaction notes
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