Hydrochloric Acid → HCID 67021573, compound

HRID 1010721Notes

Reaction equation

HRID 1010721 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>C(Cl)Cl>[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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 67021624HCID 67021624, compound

Product 1

HCID 67021573HCID 67021573, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 1.0 g of [4-(2-nitro-phenylamino)-phenyl]-acetic acid and 0.4 ml of HCl conc. in 20 ml of MeOH is stirred and refluxed for 1 hour. The mixture obtained is allowed to cool to rt, and is concentrated in vacuo. The concentrate obtained is diluted with CH2Cl2, the mixture obtained is washed with an aqueous saturated solution of NaHCO3, H2O, and brine, dried (Na2SO4), filtered and concentrated. The concentrate obtained is subjected to silica gel column chromatography. [4-(2-Nitro-phenylamino)-phenyl]-acetic acid methyl ester is obtained in the form of an 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 hour
  2. customThe mixture obtained
  3. concentrationis concentrated in vacuo
  4. customThe concentrate obtained
  5. customthe mixture obtained
  6. washis washed with an aqueous saturated solution of NaHCO3, H2O, and brine
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe concentrate obtained

Sources & evidence

ORD record
ord-9945e51c05204760a858d05f7569fda3
Source dataset
uspto-grants-2011_07
Patent number
US07977338B2

Reaction notes

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