Hydrochloric Acid → (2-Amino-5-chloro-3-nitrophenyl)methanol

HRID 1012117Notes

Reaction equation

HRID 1012117 reaction equation
C([NH:4][C:5]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([Cl:19])=[CH:12][C:6]=1[CH2:7][O:8]C(=O)C)(=O)C.[OH-].[Na+].Cl>CO.O>[NH2:4][C:5]1[C:15]([N+:16]([O-:18])=[O:17])=[CH:14][C:13]([Cl:19])=[CH:12][C:6]=1[CH2:7][OH:8]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67106404(2-Acetamido-5-chloro-3-nitrophenyl)methyl acetate

Product 1

HCID 67106330(2-Amino-5-chloro-3-nitrophenyl)methanolYield 260%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

Acetic acid 2-acetylamino-5-chloro-3-nitro-benzyl ester (0.454 g, 0.45 mmol) and sodium hydroxide (0.436 g, 11 mmol) were dissolved in methanol-water (1:3, 40 ml) and the resulting solution heated at reflux for 5 h. After cooling the mixture was taken to pH 6 by the addition of conc. HCl. The precipitate formed was collected by filtration to give (2-amino-5-chloro-3-nitro-phenyl)-methanol as a dark orange solid (0.237 g, 73%). (LC/MS: Rt 2.63, [M−H]− 200.96).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureat reflux for 5 h
  3. temperatureAfter cooling the mixture
  4. customThe precipitate formed
  5. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-7cef3bf2bfdb4876bd969a4daac19769
Source dataset
uspto-grants-2011_07
Patent number
US07977477B2

Reaction notes

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