Acetic Acid → Methyl 4-(6-amino-3-benzyloxyindazol-1-ylmethyl)-3-methoxybenzoate

HRID 1756411Notes

Reaction equation

HRID 1756411 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[C:12](=[CH:13][C:14]([N+:18]([O-])=O)=[CH:15][CH:16]=2)[N:11]([CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=2[O:32][CH3:33])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)(=O)C>CCOCC.[Zn]>[NH2:18][C:14]1[CH:13]=[C:12]2[C:17]([C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[N:10][N:11]2[CH2:21][C:22]2[CH:31]=[CH:30][C:25]([C:26]([O:28][CH3:29])=[O:27])=[CH:24][C:23]=2[O:32][CH3:33])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 23365833Methyl 4-(3-benzyloxy-6-nitroindazol-1-ylmethyl)-3-methoxybenzoate

Product 1

HCID 23365892Methyl 4-(6-amino-3-benzyloxyindazol-1-ylmethyl)-3-methoxybenzoateYield 85%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolvent

Procedure

Zinc dust (0.065 g.) was added to a stirred mixture of methyl 4-(3-benzyloxy-6-nitroindazol-1-ylmethyl)-3-methoxybenzoate (CC) (0.043 g.) and acetic acid (0.9 ml.). The mixture was stirred for 2 hours, diluted with ether, and filtered. The filtrate was washed with water, brine, dried (MgSO4), and evaporated to give methyl 4-(6-amino-3-benzyloxyindazol-1-ylmethyl)-3-methoxybenzoate (DD) (0.034 g., 85%) as a brown oil, and was used without further purification as described below.

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with water, brine
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-88b3172e84ef4c529e1b1003b94ae117
Source dataset
uspto-grants-1995_08
Patent number
US05440035

Reaction notes

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