Ammonia → 2-Amino-3-nitro-8-methylquinoline

Reaction equation

Cl[C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[NH3:16]>>[NH2:16][C:2]1[C:11]([N+:12]([O-:14])=[O:13])=[CH:10][C:9]2[C:4](=[C:5]([CH3:15])[CH:6]=[CH:7][CH:8]=2)[N:3]=1

Participants

Reactant 2

HCID 222Ammonia

HCID 17979837HCID 17979837, compound2×

Product 1

HCID 179798462-Amino-3-nitro-8-methylquinoline

Conditions

Temperature: 130 °C

Procedure

1.6 g of 2-chloro-8-methyl-3-nitroquinoline (compound C1) is dissolved in 70 ml of ethanolic ammonia solution and stirred at 130° C. for 18 h in an autocave. After cooling to room temperature, the reaction mixture is concentrated in vacuo and the residue recrystallized from ethyl acetate. 1.2 g of the title compound are obtained as red solid.

Workup

temperatureAfter cooling to room temperature
concentrationthe reaction mixture is concentrated in vacuo
customthe residue recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-8138eba8947d4b7c8a83e99ea616d2eb
Source dataset: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07390819B2

Reaction notes

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