Acetic Acid → 4-(4-Hydroxymethyl-2-methylanilino)-6,7-dimethoxy-3-quinolinecarboxamide
Reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][C:12]=1[O:13][CH3:14])[N:9]=[CH:8][C:7]([C:15]([NH2:17])=[O:16])=[C:6]2[NH:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](OC)=[O:26])=[CH:21][C:20]=1[CH3:29].[BH4-].[Li+].O.C(O)(=O)C>O1CCCC1>[OH:26][CH2:25][C:22]1[CH:23]=[CH:24][C:19]([NH:18][C:6]2[C:5]3[C:10](=[CH:11][C:12]([O:13][CH3:14])=[C:3]([O:2][CH3:1])[CH:4]=3)[N:9]=[CH:8][C:7]=2[C:15]([NH2:17])=[O:16])=[C:20]([CH3:29])[CH:21]=1Participants
6
Procedure
6,7-Dimethoxy-4-(4-methoxycarbonyl-2-methylanilino)-3-quinolinecarboxamide (0.080 g, 0.20 mmol) was dissolved in tetrahydrofuran (25 ml, dried over 4 A molecular sieves). Lithium borohydride (0.15 mg, 6.8 mmol) was added. The mixture was stirred for 24 h and additional lithium borohydride (0.050 g, 2.2 mmol) was added. The reaction mixture was stirred for additional 25 h and then poured into a cooled mixture of water (20 ml) and acetic acid (0.5 ml). Acetic acid (2 ml) was added and the mixture was evaporated under reduced pressure. The residue was suspended in water, filtered and the precipitate was washed with water and re-crystallized from aqueous methanol to give the title compound (32 mg, 43%).
Workup
- customdried over 4 A molecular sieves)
- stirringThe reaction mixture was stirred for additional 25 h
- customthe mixture was evaporated under reduced pressure
- filtrationfiltered
- washthe precipitate was washed with water
- customre-crystallized from aqueous methanol
Sources & evidence
- ORD record
- ord-db4a0051cd6745c88018d5812e9fbb3b
- Source dataset
- uspto-grants-2006_05
- Patent number
- US07037925B2
Reaction notes
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