Ammonia → 4-Hydroxy-3-nitrobenzamide

HRID 2060041Notes

Reaction equation

HRID 2060041 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6](OC)=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH3:15].Cl>O>[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH2:15])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 66835Benzoic acid, 4-hydroxy-3-nitro-, methyl ester

Product 1

HCID 118496324-Hydroxy-3-nitrobenzamideYield 53.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of methyl 4-hydroxy-3-nitrobenzoate (1.00 g, 5.07 mmol) and concentrated aq ammonia (10.0 mL, 162 mmol) was heated to 100° C. for 90 mins (3×30 mins) in a microwave reactor. The mixture was poured into water (70 mL), acidified with 6N HCl and extracted with EtOAc (4×25 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo. The residue was triturated with DCM (20 mL) filtered and washed with DCM before drying under vacuum to afford the crude title compound as a yellow solid 0.49 g, 53.0%

Workup

  1. extractionextracted with EtOAc (4×25 mL)
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customThe residue was triturated with DCM (20 mL)
  5. filtrationfiltered
  6. washwashed with DCM
  7. custombefore drying under vacuum

Sources & evidence

ORD record
ord-8e1ecd0a36a841fbaedc53fcacc9b170
Source dataset
uspto-grants-2012_10
Patent number
US08278328B2

Reaction notes

Loading…