Methyl 3-methoxy-4-[(6-nitroindazol-2-yl)methyl]benzoate → Methyl 4-[(6-aminoindazol-2-yl)methyl]benzoate

HRID 1753346Notes

Reaction equation

HRID 1753346 reaction equation
CC(OC1C=CC=C([N+]([O-])=O)C=1)(C(OCC)=O)C(OCC)=O.CO[C:25]1[CH:26]=[C:27]([CH:32]=[CH:33][C:34]=1[CH2:35][N:36]1[CH:44]=[C:43]2[C:38]([CH:39]=[C:40]([N+:45]([O-])=O)[CH:41]=[CH:42]2)=[N:37]1)[C:28]([O:30][CH3:31])=[O:29]>>[NH2:45][C:40]1[CH:41]=[CH:42][C:43]2[C:38]([CH:39]=1)=[N:37][N:36]([CH2:35][C:34]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1)[CH:44]=2

Participants

3

Reactant 2

HCID 14708759Methyl 3-methoxy-4-[(6-nitroindazol-2-yl)methyl]benzoateHCID 22060402Diethyl 2-methyl-2-(3-nitrophenoxy)malonate

Product 1

HCID 22060705Methyl 4-[(6-aminoindazol-2-yl)methyl]benzoate

Procedure

In like manner to the reduction of diethyl 2-methyl-2-(3-nitrophenoxy)malonate, methyl 3-methoxy-4-[(6-nitroindazol-2-yl)methyl]benzoate was reduced to provide methyl 4-[(6-aminoindazol-2-yl)methyl]benzoate. 1H NMR (CDCl3): δ 7.78 (s, 1H), 7.56-7.53 (m, 2H), 7.43 (d, 1H, J=8.8 Hz), 6.98 (d, 1H, J=8.2 Hz), 6.81 (app s, 1H), 6.58 (dd, 1H, J=1.8 and 8.8 Hz), 5.53 (s, 2H), 3.91 (s, 3H), 3.89 (s, 3H).

Sources & evidence

ORD record
ord-7952a763ba0641338798bf3226c878c6
Source dataset
uspto-grants-2015_10
Patent number
US09162989B2

Reaction notes

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