2-Chloro-5-nitrobenzoic acid → HCID 59163380, compound

HRID 1879115Notes

Reaction equation

HRID 1879115 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.[NH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:17][CH:16]=1>S(Cl)(Cl)=O.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:19][CH:20]=1)=[O:6]

Participants

5

Reactant 2

HCID 172872-Chloro-5-nitrobenzoic acidHCID 225219p-Aminophenylacetic acid ethyl ester

Product 1

HCID 59163380HCID 59163380, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

2-Chloro-5-nitrobenzoic acid (1.99 g, 9.87 mmol) was stirred for 18 hrs at 60° C. in thionyl chloride (10 ml). The excess thionyl chloride was removed by evaporation and the crude oil dissolved in chloroform (20 ml). To this solution was added ethyl (4-aminophenyl)acetate (1.18 g, 6.58 mmol) and the reaction was stirred at 60° C. for 18 hrs. The reaction was diluted with water and the phases separated. The organic layer was dried (Na2SO4), solvent evaporated and the residue purified by flash chromatography (Biotage SP4, 40+M 0→50% ethylacetate/hexane) to afford the title compound as an off white solid (2.28 g, 96%).

Workup

  1. customThe excess thionyl chloride was removed by evaporation
  2. dissolutionthe crude oil dissolved in chloroform (20 ml)
  3. customthe phases separated
  4. dry with materialThe organic layer was dried (Na2SO4), solvent
  5. customevaporated
  6. customthe residue purified by flash chromatography (Biotage SP4, 40+M 0→50% ethylacetate/hexane)

Sources & evidence

ORD record
ord-855e69304c1748b8814aae29af66c7e1
Source dataset
uspto-grants-2012_11
Patent number
US08314147B2

Reaction notes

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