4-Nitroaniline → ethyl {2-[(4-nitrophenyl)amino]-3H-imidazo[4,5-b]pyridin-3-yl}acetate

HRID 587595Notes

Reaction equation

Cl[C:2]1[N:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[N:3]=1.[N+:17]([C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1)([O-:19])=[O:18]>>[N+:17]([C:20]1[CH:26]=[CH:25][C:23]([NH:24][C:2]2[N:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[N:3]=2)=[CH:22][CH:21]=1)([O-:19])=[O:18]

Participants

Reactant 2

HCID 74754-Nitroaniline

HCID 58577766HCID 58577766, compound

Product 1

HCID 70168453ethyl {2-[(4-nitrophenyl)amino]-3H-imidazo[4,5-b]pyridin-3-yl}acetateYield 101.2%

Conditions

Temperature: 150 °C

Procedure

A mixture of ethyl (2-chloro-3H-imidazo[4,5-b]pyridin-3-yl)acetate (2.8 g) and 4-nitroaniline (1.6 g) was stirred at 150° C. for 1 h to give the title compound (4.0 g).

Sources & evidence

ORD record: ord-84e346f135e4437b9e1b2b8aad98de7e
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09226921B2

Reaction notes

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