HCID 178526874, compound → HCID 178508078, compound

HRID 389058Notes

Reaction equation

HRID 389058 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([N+:19]([O-])=O)=[C:17]([OH:22])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:23]([O:30][C:31]1[C:40]([N+:41]([O-])=O)=[C:39]([OH:44])[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][N:37]=2)[N:32]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[NH2:19][C:18]1[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)=[N:10][C:11]2[C:16]([C:17]=1[OH:22])=[CH:15][CH:14]=[CH:13][CH:12]=2.[NH2:41][C:40]1[C:31]([O:30][CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:32][C:33]2[C:38]([C:39]=1[OH:44])=[N:37][CH:36]=[CH:35][CH:34]=2

Participants

4

Reactant 2

HCID 178526874HCID 178526874, compoundHCID 178526875HCID 178526875, compound

Product 2

HCID 178508078HCID 178508078, compoundHCID 178508079HCID 178508079, compound

Procedure

In step (4) of Reaction Scheme V, a benzyloxy-3-nitroquinolin-4-ol or benzyloxy-3-nitro[1,5]naphthyridin-4-ol of Formula XLVI is reduced to provide a 3-amino-benzyloxyquinolin-4-ol or 3-aminobenzyloxy[1,5]naphthyridin-4-ol of Formula XLVII. The reaction can be carried out by hydrogenation using a heterogeneous hydrogenation catalyst such as platinum on carbon. The hydrogenation is conveniently carried out in a Parr apparatus in a suitable solvent such as dimethylformamide (DMF). The reaction can be carried out at ambient temperature, and the product or the hydrochloride salt thereof can be isolated using conventional methods.

Workup

  1. customIn step (4) of Reaction Scheme V

Sources & evidence

ORD record
ord-08fdadd3f27e456e81232df6f47f681d
Source dataset
uspto-grants-2013_02
Patent number
US08378102B2

Reaction notes

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