Hydrochloric Acid → HCID 69412799, compound

HRID 1373483Notes

Reaction equation

HRID 1373483 reaction equation
[Na].[OH:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.CS(O[CH2:24][CH2:25][CH2:26][O:27][C:28]1[CH:37]=[CH:36][C:35]2[C:30](=[C:31]([CH2:38][CH2:39][NH:40][C:41](=[O:43])[CH3:42])[CH:32]=[CH:33][CH:34]=2)[CH:29]=1)(=O)=O.Cl>O.CO>[C:41]([NH:40][CH2:39][CH2:38][C:31]1[CH:32]=[CH:33][CH:34]=[C:35]2[C:30]=1[CH:29]=[C:28]([O:27][CH2:26][CH2:25][CH2:24][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]3[CH:14]=[CH:13][C:12]([C:15]([O:17][CH3:18])=[O:16])=[CH:11][CH:10]=3)=[CH:7][CH:8]=1)[CH:37]=[CH:36]2)(=[O:43])[CH3:42]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1490289Methyl 4'-hydroxy(1,1'-biphenyl)-4-carboxylateHCID 5360545Sodium2×HCID 15486877HCID 15486877, compound

Product 1

HCID 69412799HCID 69412799, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

In a 100 ml round-bottomed flask containing 30 ml of methanol, 0.06 g of sodium is added in small portions. When the sodium has been completely used up, 0.0033 mol of methyl 4′-hydroxy[1,1′-biphenyl]-4-carboxylate is added and the mixture is stirred for 20 minutes. The methanol is removed by evaporation under reduced pressure, the residue is taken up in 15 ml of DMF, and then 0.0027 mol of the compound obtained in Step B is added. The reaction mixture is then heated at reflux for 12 hours and subsequently cooled and poured into 100 ml of water and 10 ml of 3M HCl. After extraction with ethyl acetate, the organic phase is washed with a 10% sodium hydroxide solution and then with water. After drying over MgSO4 and removal of the solvent by evaporation under reduced pressure, the title compound is purified by chromatography on silica gel.

Workup

  1. additionis added in small portions
  2. customThe methanol is removed by evaporation under reduced pressure
  3. temperatureThe reaction mixture is then heated
  4. temperatureat reflux for 12 hours
  5. temperaturesubsequently cooled
  6. extractionAfter extraction with ethyl acetate
  7. washthe organic phase is washed with a 10% sodium hydroxide solution
  8. dry with materialAfter drying over MgSO4 and removal of the solvent by evaporation under reduced pressure
  9. customthe title compound is purified by chromatography on silica gel

Sources & evidence

ORD record
ord-257220855e6c487985730ae515295739
Source dataset
uspto-grants-2007_01
Patent number
US07161035B2

Reaction notes

Loading…