2-Amino-5-nitrobenzoic acid → 2-Amino-5-nitrobenzyl alcohol

HRID 625897Notes

Reaction equation

HRID 625897 reaction equation
[N+:1]([C:4]1[CH:12]=[C:8]([C:9](O)=[O:10])[C:7]([NH2:13])=[CH:6][CH:5]=1)([O-:3])=[O:2]>C1COCC1>[OH:10][CH2:9][C:8]1[CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=[CH:6][C:7]=1[NH2:13]

Participants

3

Reactant 1

HCID 120322-Amino-5-nitrobenzoic acid

Product 1

HCID 30187062-Amino-5-nitrobenzyl alcoholYield 234%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

5-Nitroanthranilic acid (5.0 g, 27.45 mmol) is dissolved in THF (100 mL) and 1 M borane/THF complex (55 mL, 54.9 mmol) is added. The mixture is heated to reflux for 1 h. Analysis by TLC indicates complete consumption of starting material. The volatiles are removed in vacuo and the residue is dissolved in ethyl acetate (150 mL). The organic phase is washed with 1 N HCl, saturated NaHCO3, and saturated NaCl. Evaporation provides 10.8 g (98%) of a dark brown oil product which is used directly in the next reaction; 1H-NMR (500 MHz, CDCl3); δ 4.61 (s, 2 H), 6.62 (s, 1 H), 8.01 (m, 2 H).

Workup

  1. addition1 M borane/THF complex (55 mL, 54.9 mmol) is added
  2. temperatureThe mixture is heated
  3. temperatureto reflux for 1 h
  4. customconsumption of starting material
  5. customThe volatiles are removed in vacuo
  6. dissolutionthe residue is dissolved in ethyl acetate (150 mL)
  7. washThe organic phase is washed with 1 N HCl, saturated NaHCO3, and saturated NaCl
  8. customEvaporation

Sources & evidence

ORD record
ord-f9b28505f19e47968a3c0abecc0cb15e
Source dataset
uspto-grants-2016_04
Patent number
US09309185B2

Reaction notes

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