Triethylamine → HCID 178498802, compound

HRID 2267085Notes

Reaction equation

HRID 2267085 reaction equation
[CH2:1]([O:8][C:9]1[C:10]([CH3:17])=[N:11][CH:12]=[C:13](Br)[C:14]=1[OH:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[C]=O.[Cl-].[NH4+].[C:58]([O:61][CH2:62]C)(=[O:60])C>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O.CO>[CH3:62][O:61][C:58](=[O:60])[C:13]1[C:14]([OH:15])=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:10]([CH3:17])=[N:11][CH:12]=1

Participants

11

Reactant 6

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 812191,3-Bis(diphenylphosphino)propaneHCID 178418416HCID 178418416, compoundHCID 178432655HCID 178432655, compound

Product 1

HCID 178498802HCID 178498802, compoundYield 55%

Reagents, catalysts & solvents 4

HCID 167845palladium(II) acetateCatalystHCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of the compound 4 (88 g, 300 mmol), palladium acetate (13.4 g, 60 mmol) and 1,3-bis(diphenylphosphino)propane (30.8 g, 516 mmol) in dimethylformamide (660 ml) were added methanol (264 ml) and triethylamine (210 ml, 1.5 mol) at room temperature. The interior of a reaction vessel was replaced with carbon monoxide, and the material was stirred at room temperature for 30 minutes, and stirred at 80 degree for 18 hours. A vessel to which ethyl acetate (1500 ml), an aqueous saturated ammonium chloride solution (1500 ml) and water (1500 ml) had been added was stirred under ice-cooling, and the reaction solution was added thereto. Precipitates were filtered, and washed with water (300 ml), ethyl acetate (300 ml) and diethyl ether (300 ml) to obtain 5-benzyloxy-4-hydroxy-6-methyl-nicotinic acid methyl ester 5 (44.9 g, 55%) as a colorless crystal.

Workup

  1. stirringstirred at 80 degree for 18 hours
  2. stirringwas stirred under ice-
  3. temperaturecooling
  4. additionthe reaction solution was added
  5. customPrecipitates
  6. filtrationwere filtered
  7. washwashed with water (300 ml), ethyl acetate (300 ml) and diethyl ether (300 ml)

Sources & evidence

ORD record
ord-ade4e8928d9046a1b3988215423e706b
Source dataset
uspto-grants-2010_12
Patent number
US07858788B2

Reaction notes

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