Sodium Bicarbonate → 2-Benzyloxy-3-nitroaniline

HRID 1064843Notes

Reaction equation

C(OC([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[C:10]=1[O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=O)(C)(C)C.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>CO>[CH2:19]([O:18][C:10]1[C:11]([N+:15]([O-:17])=[O:16])=[CH:12][CH:13]=[CH:14][C:9]=1[NH2:8])[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 50 °C

Procedure

N-tert-Butoxycarbonyl-2-benzyloxy-3-nitroaniline (9.37 g, 27.2 mmol) was dissolved in methanol (150 ml), p-toluenesulfonic acid monohydrate (7.84 g, 45.5 mmol) was added thereto and the mixture was stirred at 50° C. for 12 hours. The reaction solution was neutralized with a saturated aqueous solution of sodium bicarbonate and extracted with chloroform. The organic layer was washed with water and a saturated sodium chloride solution successively and dried over anhydrous sodium sulfate and the solvent was evaporated. The residue was purified by a silica gel column chromatography (50 g of silica gel; developing solvent, hexane:ethyl acetate=6:1) to provide 6.44 g (yield 96.9%) of 2-benzyloxy-3-nitroaniline as pale yellowish brown oil.

Workup

extractionextracted with chloroform
washThe organic layer was washed with water
dry with materiala saturated sodium chloride solution successively and dried over anhydrous sodium sulfate
customthe solvent was evaporated
customThe residue was purified by a silica gel column chromatography (50 g of silica gel; developing solvent, hexane:ethyl acetate=6:1)

Sources & evidence

ORD record: ord-e7b2917423a448aabfbbb15cc96cb189
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969711B2

Reaction notes

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