Methyl 3-methoxy-4-(6-nitrobenzimidazol-1-ylmethyl)benzoate → Methyl 4-(6-aminobenzimidazol-1-ylmethyl)-3-methoxybenzoate

HRID 1080780Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:12]=1[CH2:13][N:14]1[C:18]2[CH:19]=[C:20]([N+:23]([O-])=O)[CH:21]=[CH:22][C:17]=2[N:16]=[CH:15]1)[C:6]([O:8][CH3:9])=[O:7]>C(O)C.C(OCC)(=O)C>[NH2:23][C:20]1[CH:21]=[CH:22][C:17]2[N:16]=[CH:15][N:14]([CH2:13][C:12]3[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=3[O:2][CH3:1])[C:18]=2[CH:19]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of (K) (0.77 g.) in anhydrous ethanol (23 ml.) was treated with stannous chloride dihydrate (2.6 g.). The mixture was stirred for 18 hours at 80° C. and then diluted with ethyl acetate. This mixture was washed successively with saturated sodium bicarbonate solution, water, and brine, then dried (MgSO4) and evaporated to give methyl 4-(6-aminobenzimidazol-1-ylmethyl)-3-methoxybenzoate (J) (0.63 g., 90%): partial NMR: 3.4(br s, 2H, NH2), 5.2(s,2H, NCH2).

Workup

washThis mixture was washed successively with saturated sodium bicarbonate solution, water, and brine
dry with materialdried (MgSO4)
customevaporated

Sources & evidence

ORD record: ord-e5ec32472f1b4d9c9d343551cabe409d
Source dataset: uspto-grants-1996_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05583152

Reaction notes

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