N-hydroxymethyl dichloroacetamide → 1-(1-Ethylpropyl)-5-dichloroacetylaminomethylisoquinoline
Reaction equation
[CH2:1]([CH:3]([C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][N:7]=1)[CH2:4][CH3:5])[CH3:2].O[CH2:17][NH:18][C:19](=[O:23])[CH:20]([Cl:22])[Cl:21]>>[CH2:1]([CH:3]([C:6]1[C:15]2[C:10](=[C:11]([CH2:17][NH:18][C:19](=[O:23])[CH:20]([Cl:22])[Cl:21])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][N:7]=1)[CH2:4][CH3:5])[CH3:2]Participants
3
Procedure
1-(1-Ethylpropyl)isoquinoline and N-hydroxymethyl dichloroacetamide were reacted in the same way as in step (b) of Example 18 to afford 1-(1-ethylpropyl)-5-dichloroacetylaminomethylisoquinoline. The product was successively reacted in the same way as in steps (c), (d), (e) and (f) of Example 18 to afford 1-(1-ethylpropyl)-isoquinoline-5-acetonitrile. The product was treated in the same way as in Example 3 to afford 1-(1-ethylpropyl)-isoquinoline-5-acetic acid as an oil. The hydrochloride of the product was in the form of colorless prisms having a melting point of 107° to 109° C.
Sources & evidence
- ORD record
- ord-1612c50d774f4ebfb992fa4e08cd96e8
- Source dataset
- uspto-grants-1982_06
- Patent number
- US04337256
Reaction notes
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