6-Bromo-7-fluoro-N-(4-methyloxan-4-yl)-3-nitroquinolin-4 amine → 6-Bromo-7-fluoro-N'-(4-methyloxan-4-yl)quinoline-3,4-diamine

HRID 1486938Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[CH:7][C:6]([N+:13]([O-])=O)=[C:5]2[NH:16][C:17]1([CH3:23])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1>C(O)(=O)C.[Fe]>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][C:11]=1[F:12])[N:8]=[CH:7][C:6]([NH2:13])=[C:5]2[NH:16][C:17]1([CH3:23])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 60 °C

Procedure

6-Bromo-7-fluoro-N-(4-methyloxan-4-yl)-3-nitroquinolin-4 amine (1.215 g, 3.16 mmol) was added to iron powder (1.8 g) in acetic acid (15 mL). The mixture was stirred and heated gently with a hot air gun (approximately 60° C.) to initiate reaction. The heat source was removed and the resulting mixture was stirred for 1 h. The reaction mixture was diluted with water and the solids removed by filtration and discarded. The filtrate was concentrated in vacuo, diluted with water and extracted with EtOAc. The organics were dried over Na2SO4 and concentrated in vacuo to afford the desired material (1.10 g, 98%) as a brown solid which was used without further purification.

Workup

customreaction
customThe heat source was removed
stirringthe resulting mixture was stirred for 1 h
additionThe reaction mixture was diluted with water
customthe solids removed by filtration
concentrationThe filtrate was concentrated in vacuo
additiondiluted with water
extractionextracted with EtOAc
dry with materialThe organics were dried over Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-425f12f275ea42408bc455b7baec4b3a
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09428503B2

Reaction notes

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