Ammonium → 2-Chloroquinolin-6-amine

HRID 2366357Notes

Reaction equation

HRID 2366357 reaction equation
[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([N+:12]([O-])=O)[CH:8]=2)[N:3]=1.[NH4+]>C(O)C.O.[Fe]>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([NH2:12])[CH:8]=2)[N:3]=1

Participants

6

Reactant 2

HCID 223AmmoniumHCID 109217232-Chloro-6-nitroquinoline

Product 1

HCID 154450542-Chloroquinolin-6-amine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

2-chloro-6-nitro-quinoline (12.5 g, 59.9 mmol) and ammonium chloridel (9.78 g, 183 mmol) were suspended in ethanol (175 mL) and water (50 mL). The resulting mixture was heated to 60° C. and iron powder (15.06 g, 270 mmol) was added as a solid in portions. The reaction mixture was stirred at 60° C. for 2 hours. LC-MS at this point showed one major peak corresponding to desired product. The reaction mixture was then concentrated to remove the majority of ethanol, and the residue was diluted with ethyl acetate and filtered to remove brown solids. The filter cake was washed with ethyl acetate. The filtrate was then dried over MgSO4, filtered and concentrated to afford a brown solid. This material was adsorbed onto silica and purified via Biotage automated flash column chromatography, eluting with 10-100% ethyl acetate/heptane. Relevant fractions were pooled and concentrated to afford a creamy yellow soft fluffy solid, which was dried under high vacuum to provide 6.45 g (60% yield) of product.

Sources & evidence

ORD record
ord-5a6fc2409d2942859e94798bb6ade0cd
Source dataset
uspto-grants-2014_04
Patent number
US08697739B2

Reaction notes

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