Methyl 3-methoxy-4-[(6-nitroindazol-1-yl)methyl]benzoate → Methyl 4-(6-aminoindazol-1-ylmethyl)benzoate

HRID 1829265Notes

Reaction equation

HRID 1829265 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[C:44]2[C:39](=[CH:40][CH:41]=[C:42]([N+:45]([O-])=O)[CH:43]=2)[CH:38]=[N:37]1)[C:28]([O:30][CH3:31])=[O:29]>>[NH2:45][C:42]1[CH:43]=[C:44]2[C:39]([CH:38]=[N:37][N:36]2[CH2:35][C:34]2[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=2)=[CH:40][CH:41]=1

Participants

3

Reactant 2

HCID 14708758Methyl 3-methoxy-4-[(6-nitroindazol-1-yl)methyl]benzoateHCID 22060402Diethyl 2-methyl-2-(3-nitrophenoxy)malonate

Product 1

HCID 14708763Methyl 4-(6-aminoindazol-1-ylmethyl)benzoate

Procedure

In like manner to the reduction of diethyl 2-methyl-2-(3-nitrophenoxy)malonate, methyl 3-methoxy-4-[(6-nitroindazol-1-yl)methyl]benzoate was reduced to provide methyl 4-[(6-aminoindazol-1-yl)methyl]benzoate. 1H NMR (CDCl3): δ 7.88 (s, 1H), 7.53 (d, 1H, J=8.8 Hz), 7.51 (d, 1H, J=8.8 Hz), 7.50 (d, 1H, J=1.7 Hz), 6.67 (d, 1H, J=8.8 Hz), 6.56 (dd, 1H, J=1.7 and 8.8 Hz), 6.45 (d, 1H, J=1.2 Hz), 5.50 (s, 2H), 3.94 (s, 3H), 3.87 (s, 3H), 3.79 (br s, 2H).

Sources & evidence

ORD record
ord-259431efbf684c4a817f03ffe013d7f5
Source dataset
uspto-grants-2006_06
Patent number
US07060827B2

Reaction notes

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