Water → HCID 59474959, compound

HRID 2036551Notes

Reaction equation

HRID 2036551 reaction equation
C[O:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1.[Cl-].[Al+3].[Cl-].[Cl-].O>ClCCl>[OH:2][C:3]1[CH:11]=[CH:10][C:6]([C:7]([NH2:9])=[O:8])=[C:5]([N+:12]([O-:14])=[O:13])[CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1185584-Methoxy-2-nitrobenzene-1-carboximidic acidHCID 6451240Aluminum(III) Chloride

Product 1

HCID 59474959HCID 59474959, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxy-2-nitrobenzamide 2 (1.0 g, 0.005 mol) in 20 mL dichloromethane cooled in an ice-bath was added aluminum chloride (2.0 g, 0.015 mol) portion wise. The resulting mixture was gradually warmed to room temperature and then refluxed for 6 h. The progress of the reaction was monitored by thin layer chromatography (TLC). The reaction mixture was added to water. The aqueous layer was separated and evaporated to dryness. The residue was dissolved in methyl tert-butyl ether, filtered and the filtrate was evaporated to give 4-hydroxy-2-nitrobenzamide 3. Colorless oil (0.7 g, 75%). 1H NMR (400 MHz, CDCl3): δ 7.07 (dd, J=2.4, 8.4 Hz, 1H); 7.32 (d, J=2.4 Hz, 1H); 7.45 (d, J=8.4 Hz, 1H).

Workup

  1. temperaturerefluxed for 6 h
  2. customThe aqueous layer was separated
  3. customevaporated to dryness
  4. dissolutionThe residue was dissolved in methyl tert-butyl ether
  5. filtrationfiltered
  6. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-a80e607095cb42dba56ca150dafd8709
Source dataset
uspto-grants-2013_11
Patent number
US08575185B2

Reaction notes

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