Nitric Acid → HCID 20060121, compound

HRID 1088679Notes

Reaction equation

HRID 1088679 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[NH:17][C:16](=[O:18])[NH:15][C:11]3=[N:12][C:13]=2[CH3:14])=[CH:4][CH:3]=1.[N+:19]([O-])([OH:21])=[O:20]>>[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[NH:17][C:16](=[O:18])[NH:15][C:11]3=[N:12][C:13]=2[CH3:14])=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20]

Participants

3

Reactant 2

HCID 944Nitric AcidHCID 14822888HCID 14822888, compound

Product 1

HCID 20060121HCID 20060121, compound

Procedure

It is further contemplated that 1,3-dihydro-6(4-hydroxyphenyl)-5-methyl-2H-imidazo[4,5-b]pyridin-2-one (Example 16) can be nitrated with nitric acid to obtain 6-(4-hydroxy-3-nitrophenyl)-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one [I; Ar 3-O2N-4-HOC6H3, R1 and R3 =H, R5 =CH3 ], which in turn can be reduced by catalytic hydrogenation to obtain 6-(3-amino-4-hydroxyphenyl)-1,3-dihydro-5-methyl-2H-imidazo[4,5-b]pyridin-2-one I; Ar =3-H2N-4-HOC6H3, R1 and R3 =H, R5 =CH3 ].

Sources & evidence

ORD record
ord-5fc73439abaa40a28916e879e0941c67
Source dataset
uspto-grants-1990_10
Patent number
US04963561

Reaction notes

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