2-Chloropropyldimethylamine → 9-fluoro-2-[4-(1-methyl-2-dimethylaminoethoxy)phenyl]-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one
Reaction equation
[F:1][C:2]1[CH:23]=[CH:22][C:5]2[CH2:6][CH2:7][CH:8]3[C:13]([C:4]=2[CH:3]=1)=[N:12][N:11]([C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)[C:10](=[O:21])[CH2:9]3.[CH3:24][CH:25](Cl)[CH2:26][N:27]([CH3:29])[CH3:28].C([O-])(=O)/C=C/C([O-])=O>>[F:1][C:2]1[CH:23]=[CH:22][C:5]2[CH2:6][CH2:7][CH:8]3[C:13]([C:4]=2[CH:3]=1)=[N:12][N:11]([C:14]1[CH:19]=[CH:18][C:17]([O:20][CH:25]([CH3:24])[CH2:26][N:27]([CH3:29])[CH3:28])=[CH:16][CH:15]=1)[C:10](=[O:21])[CH2:9]3Participants
Procedure
By conducting reactions and treatments in the same manner as in Example 1 using 9-fluoro-2-(4-hydroxyphenyl)-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one and 1-methyl-2-dimethylaminoethyl chloride, there are obtained crude crystals, which are subjected to silica gel column chromatography. The crystals obtained from fractions at earlier stage are converted into fumarate, followed by recrystallization from ethanol to give 9-fluoro-2-[4-(1-methyl-2-dimethylaminoethoxy)phenyl]-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one.fumarate.1/2 hydrate [referred to as compound of Example 11a], m.p. 176°-179° C. (decomposition). The crystals obtained from fractions at later stage are converted into fumarate, which is recrystallized from water to give 9-fluoro-2-[4-(2-dimethylaminopropoxy)phenyl]-4,4a,5,6-tetrahydrobenzo[h]cinnolin-3(2H)-one.fumarate [referred to as compound of Example 11b], m.p. 194°-195° C.
Workup
- customare obtained crude crystals, which
- customThe crystals obtained from fractions at earlier stage
- customfollowed by recrystallization from ethanol
Sources & evidence
- ORD record
- ord-3b85e6b27d6e4970a3ab7bbf0a39b3f1
- Source dataset
- uspto-grants-1991_09
- Patent number
- US05045541
Reaction notes
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