Benzyl Alcohol → (4-Amino-3-nitrophenyl)methanol

HRID 26376Notes

Reaction equation

HRID 26376 reaction equation
O=C1N=C2C=CC=CC2=[N:3]1.[H][H].Cl[C:14]1[CH:21]=[CH:20][C:17]([CH2:18][OH:19])=[CH:16][C:15]=1[N+:22]([O-:24])=[O:23].C(O)C1C=CC=CC=1>>[NH2:3][C:14]1[CH:21]=[CH:20][C:17]([CH2:18][OH:19])=[CH:16][C:15]=1[N+:22]([O-:24])=[O:23]

Participants

5

Reactant 4

HCID 244Benzyl AlcoholHCID 919334-Chloro-3-nitrobenzyl alcoholHCID 162542Benzimidazol-2-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 12902831(4-Amino-3-nitrophenyl)methanol

Procedure

The required keto benzimidazole reactants in which R4 is hydrogen can be prepared from 4-chloro-3-nitrobenzyl alcohol. The benzyl alcohol is ammoniated to give 4-amino-3-nitrobenzyl alcohol which is hydrogenated catalytically to yield 4-hydroxymethyl-o-phenylenediamine. The phenylenediamine is reacted with cyanogen bromide by the methods known to the benzimidazole art to provide 2-amino-5(6)-hydroxymethylbenzimidazole. The hydroxymethyl group of the benzimidazole compound can be oxidized with Jones reagent (a solution of chromic acid and sulfuric acid in water) to provide the corresponding 5(6)-formyl benzimidazole.

Sources & evidence

ORD record
ord-ee041935b01e40399e15fab88592797f
Source dataset
uspto-grants-1979_04
Patent number
US04150028

Reaction notes

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