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

HRID 419282

Reaction equation

HRID 419282 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 I, a benzyloxy-4-chloro-3-nitroquinoline or benzyloxy-4-chloro-3-nitro[1,5]naphthyridine of Formula XIX is treated with an amino alcohol of formula HO—(CH2)c—CH2—NH2 to provide a benzyloxy-3-nitroquinolin-4-amine or benzyloxy-3-nitro[1,5]naphthyridin-4-amine of Formula XX. The reaction is conveniently carried out by adding the amino alcohol of formula HO—(CH2)c—CH2—NH2 to a solution of a compound of Formula XIX in a suitable solvent such as dichloromethane in the presence of a tertiary amine such as triethylamine. The reaction can be carried out at ambient temperature or at an elevated temperature such as, for example, the reflux temperature of the solvent. The reaction product can be isolated using conventional methods.

Workup

  1. customIn step (5) of Reaction Scheme I

Sources & evidence

ORD record
ord-8e73153255434929bf0f88c1d544d9d9
Source dataset
uspto-grants-2012_01
Patent number
US08093390B2

Linked notes

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