Hydrochloric Acid → HCID 15640830, compound

HRID 1885351Notes

Reaction equation

HRID 1885351 reaction equation
[C:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]1[NH:16][C:15](=[O:17])[C:14]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:13][C:9]=1[C:10]([OH:12])=[O:11])#[N:2].C(=O)([O-])O.[Na+].Cl>CO.O.[Pd]>[NH2:2][CH:1]1[N:16]2[C:15](=[O:17])[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)=[CH:13][C:9]([C:10]([OH:12])=[O:11])=[C:8]2[C:4]2[S:5][CH:6]=[CH:7][C:3]1=2

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 15640829HCID 15640829, compound

Product 1

HCID 15640830HCID 15640830, compoundYield 100.5%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A suspension of 45.4 g of 2-(3-cyano-2-thienyl)-1,6-dihydro-6-oxo-5-phenylnicotinic acid in 850 ml of methanol was treated with a solution of 59.2 g of sodium hydrogen carbonate in 280 ml of water, whereupon the mixture was stirred for 45 minutes. 2.27 g of 10 percent palladium/carbon were then added thereto and the mixture was hydrogenated at room temperature. After completion of the reaction the mixture was acidified with 400 ml of 2N hydrochloric acid, the catalyst was filtered off and the filtrate was concentrated in a vacuum. After the addition of 400 ml of water, crystals separate. After stirring overnight, the mixture was suction filtered and the yellow crystals were dried. There was obtained in quantitative yield 45.9 g of 4-amino-4,6-dihydro-6-oxo-7-phenylthieno[2',3':3,4]pyrrolo[1,2-a]pyridine-9-carboxylic acid with a m.p. of 227°-235°.

Workup

  1. customwas hydrogenated at room temperature
  2. customAfter completion of the reaction the mixture
  3. filtrationthe catalyst was filtered off
  4. concentrationthe filtrate was concentrated in a vacuum
  5. additionAfter the addition of 400 ml of water, crystals
  6. customseparate
  7. stirringAfter stirring overnight
  8. filtrationfiltered
  9. customthe yellow crystals were dried

Sources & evidence

ORD record
ord-6c96930f732f4924af31e39c1eeb91c5
Source dataset
uspto-grants-1992_09
Patent number
US05143912

Reaction notes

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