Hydrochloric Acid → HCID 67021573, compound

HRID 1660964Notes

Reaction equation

HRID 1660964 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]([OH:20])=[O:19])=[CH:13][CH:12]=1)([O-:3])=[O:2].Cl.[CH3:22]O>>[CH3:22][O:19][C:18](=[O:20])[CH2:17][C:14]1[CH:15]=[CH:16][C:11]([NH:10][C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N+:1]([O-:3])=[O:2])=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 67021624HCID 67021624, compound

Product 1

HCID 67021573HCID 67021573, compound

Procedure

A mixture of [4-(2-nitro-phenylamino)-phenyl]-acetic acid (1.0 g, 3.68 mmol) and HCl conc. (0.4 mL) in MeOH (20 mL) is stirred and refluxed for 1 h, allowed to cool to rt, and concentrated in vacuo. The residue is diluted with CH2Cl2, washed with an aqueous saturated solution of NaHCO3, H2O, and brine, then dried (Na2SO4), filtered and concentrated. Silica gel column chromatography purification (Hexane/EtOAc, 4:1) of the crude product affords the title compound as a red oil: ES-MS: 287.0 [M+H]+; single peak at tR=5.01 min (System 1); Rf=0.20 (Hexane/EtOAc, 4:1).

Workup

  1. temperaturerefluxed for 1 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue is diluted with CH2Cl2
  4. washwashed with an aqueous saturated solution of NaHCO3, H2O, and brine
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customSilica gel column chromatography purification (Hexane/EtOAc, 4:1) of the crude product

Sources & evidence

ORD record
ord-a494ff0031334d14bf08b9ee6f24315b
Source dataset
uspto-grants-2011_10
Patent number
US08030311B2

Reaction notes

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