Water → 2-(Quinolin-4-ylmethylthio)pyridine-3-carboxylic acid

HRID 599360Notes

Reaction equation

HRID 599360 reaction equation
C(N(CC)CC)C.Cl[CH2:9][C:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[N:13]=[CH:12][CH:11]=1.[SH:20][C:21]1[N:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=[O:24].O>CN(C)C=O.C(OCC)(=O)C>[N:13]1[C:14]2[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:10]([CH2:9][S:20][C:21]2[C:22]([C:23]([OH:25])=[O:24])=[CH:26][CH:27]=[CH:28][N:29]=2)=[CH:11][CH:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 123557014-(Chloromethyl)quinolineHCID 178524460HCID 178524460, compound

Product 1

HCID 670539532-(Quinolin-4-ylmethylthio)pyridine-3-carboxylic acidYield 59%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Triethylamine (33 mL, 240 mmol) was added to a suspension of a mixture containing 4-(chloromethyl) quinoline (Reference Compound No. 5-1, 17.0 g) and 2-mercaptonicotinic acid (13 g, 86 mmol) in anhydrous N,N-dimethylformamide (200 mL) at room temperature, and the mixture was stirred for 48 hours. Water (700 mL) and ethyl acetate (400 mL) were added thereto. After the mixture was separated into the organic layer and the aqueous layer, 1N hydrochloric acid (50 mL) was added to the aqueous layer. The precipitated solid was filtered off and dried under reduced pressure at 60° C. to give 15 g of the title Reference Compound as a yellow solid (Yield: 59%).

Workup

  1. customAfter the mixture was separated into the organic layer
  2. additionthe aqueous layer, 1N hydrochloric acid (50 mL) was added to the aqueous layer
  3. filtrationThe precipitated solid was filtered off
  4. customdried under reduced pressure at 60° C.

Sources & evidence

ORD record
ord-457d7a41ab08491f858562b5f7087a3e
Source dataset
uspto-grants-2011_03
Patent number
US07897774B2

Reaction notes

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