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3-Hydroxybenzaldehyde → 3-[3-(2,6-Dimethylphenylamino)-6-nitroimidazo[1,2-a]pyridin-2-yl]-phenol

HRID 22798
Notes
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Reaction equation

HRID 22798 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[N+:19]#[C-:20].[OH:21][C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O>Cl(O)(=O)(=O)=O>[CH3:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH3:18])[C:13]=1[NH:19][C:20]1[N:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]2=[N:1][C:25]=1[C:24]1[CH:23]=[C:22]([OH:21])[CH:29]=[CH:28][CH:27]=1
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 1013-HydroxybenzaldehydeHCID 760092,6-Dimethylphenyl isocyanideHCID 778882-Amino-5-nitropyridine

Product 1

HCID 98643613-[3-(2,6-Dimethylphenylamino)-6-nitroimidazo[1,2-a]pyridin-2-yl]-phenol

Reagents, catalysts & solvents 1

HCID 24247Perchloric AcidSolvent

Procedure

Compound (12) was prepared according to the general synthesis instructions from 1.0 ml of 2-amino-5-nitropyridine solution (0.1 M, DCM), 0.575 ml of 2,6-dimethylphenyl isocyanide solution (0.2 M, DCM), 0.500 ml of 3-hydroxybenzaldehyde solution (0.3 M, DCM), and 10 μl of perchloric acid (w=20%).

Sources & evidence

ORD record
ord-b197a4e0af4c4b9296dbdbdd21df01ff
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06849642B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes