Hydrochloric Acid → HCID 54391473, compound

HRID 1086944Notes

Reaction equation

HRID 1086944 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH:6]=[CH:5][C:4]=1[C:17]1[CH:22]=[C:21]([C:23]([OH:25])=O)[N:20]=[C:19]([C:26]([OH:28])=[O:27])[CH:18]=1.[C:29](Cl)(=O)C(Cl)=O.Cl.[CH3:36][OH:37]>C(Cl)Cl.CN(C=O)C.O>[CH3:36][O:37][C:23]([C:21]1[CH:22]=[C:17]([C:4]2[CH:5]=[CH:6][C:7]([O:9][CH2:10][C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:8][C:3]=2[O:2][CH3:1])[CH:18]=[C:19]([C:26]([O:28][CH3:29])=[O:27])[N:20]=1)=[O:25]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 65578Oxalyl chlorideHCID 197903224-(2-Methoxy-4-benzyloxyphenyl)pyridine-2,6-dicarboxylic acid

Product 1

HCID 54391473HCID 54391473, compoundYield 65%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of 10 g (0.026 mole) of the diacid 22 in 100 ml of CH2Cl2 and 7 drops of DMF was added, at 0° C., in a dropwise fashion 12 ml (0.138 mole) of oxalyl chloride. After addition the mixture was allowed to come to room temperature with vigorous evolution of HCl gas and stirred for 2 hours. The resulting homogeneous solution was then cooled in an ice bath and 20 ml of methanol in 40 ml of CH2Cl2 was slowly added. The resulting mixture was stirred for 30 minutes at room temperature and poured into 300 ml of water. The organic phase was removed, washed with 10% NaHCO3, water, dried (Na2SO4) and solvents removed. The crude diester (15 g) was purified via plug filtration with SiO2 /EtOAc/CH2Cl2 (20:80) yielding 7.0 g (65%) of the diester (23): NMR (CDCl3) 3.85 (s,3,OCH3), 4.05 (s,6,CO2Me), 5.1 (s,2,OCH2O), 6.7 and 7.4 (m,3,--C6H3O2R2) 7.35 (s,5,--C6H5), 8.5 (s,2,--C5H2N'.

Workup

  1. additionAfter addition the mixture
  2. temperatureThe resulting homogeneous solution was then cooled in an ice bath
  3. stirringThe resulting mixture was stirred for 30 minutes at room temperature
  4. customThe organic phase was removed
  5. washwashed with 10% NaHCO3, water
  6. dry with materialdried (Na2SO4) and solvents
  7. customremoved
  8. filtrationThe crude diester (15 g) was purified via plug filtration with SiO2 /EtOAc/CH2Cl2 (20:80)

Sources & evidence

ORD record
ord-21c81ba2b96b468683f5d30384ba232e
Source dataset
uspto-grants-1991_07
Patent number
US05032677

Reaction notes

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