Hydroxylamine → Benzyloxy-3-nitro[1,5]naphthyridin-4-amine

HRID 221523

Reaction equation

HRID 221523 reaction equation
[CH2:1]([O:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17](Cl)[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-:43])=[O:42])=[C:39](Cl)[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.NO>>[CH2:1]([O:8][C:9]1[C:18]([N+:19]([O-:21])=[O:20])=[C:17]([NH2:32])[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-:43])=[O:42])=[C:39]([NH2:10])[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

Participants

5

Reactant 3

HCID 787HydroxylamineHCID 21075762Benzyloxy-4-chloro-3-nitroquinolineHCID 66650176Benzyloxy-4-chloro-3-nitro[1,5]naphthyridine

Product 2

HCID 66649873Benzyloxy-3-nitro[1,5]naphthyridin-4-amineHCID 66649911Benzyloxy-3-nitroquinolin-4-amine

Procedure

In step (5) of Reaction Scheme IV, a benzyloxy-4-chloro-3-nitroquinoline or benzyloxy-4-chloro-3-nitro[1,5]naphthyridine of Formula XXXIX is treated with an amino alcohol of Formula XVI to provide a benzyloxy-3-nitroquinolin-4-amine or benzyloxy-3-nitro[1,5]naphthyridin-4-amine of Formula XL. The reaction is conveniently carried out according to the methods described in step (1) of Reaction Scheme I.

Workup

  1. customIn step (5) of Reaction Scheme IV

Sources & evidence

ORD record
ord-80ec774466d54955a9f1f83b7908e210
Source dataset
uspto-grants-2012_06
Patent number
US08207162B2

Linked notes

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