Sodium Carbonate → N-(3-hydroxypyridin-4-yl)-5-nitrothiophene-2-carboxamide

HRID 419892Notes

Reaction equation

HRID 419892 reaction equation
[N+:1]([C:4]1[S:8][C:7]([C:9]([OH:11])=O)=[CH:6][CH:5]=1)([O-:3])=[O:2].O=S(Cl)Cl.[NH2:16][C:17]1[CH:22]=[CH:21][N:20]=[CH:19][C:18]=1[OH:23].C([O-])([O-])=O.[Na+].[Na+]>N1C=CC=CC=1.O.CC(O)=O>[OH:23][C:18]1[CH:19]=[N:20][CH:21]=[CH:22][C:17]=1[NH:16][C:9]([C:7]1[S:8][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[O:11]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 805915-Nitro-2-thenoic acidHCID 27624194-Amino-3-hydroxypyridine

Product 1

HCID 59680090N-(3-hydroxypyridin-4-yl)-5-nitrothiophene-2-carboxamideYield 78.2%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
10 °C

Procedure

A solution of 5-nitrothiophene-2carboxylic acid (5.0 g, 28.9 mmol) and SOCl2 (40 mL) was refluxed for 2 hrs. The solvent was removed in vacuo followed by addition of 4-amino-3-hydroxypyridine (2.65 g, 24.1 mmol) in pyridine (150 mL). The mixture was stirred at 10° C. overnight. Na2CO3 (1.53 g, 14.5 mmol) in water (100 mL) was added and stirred for 1 hr followed by adding AcOH to adjust pH=7. The precipitate was collected by filtration, washed with 10% AcOH (30 mL×2) and dried to give N-(3-hydroxypyridin-4-yl)-5-nitrothiophene-2-carboxamide as a yellow powder (5.0 g, yield 78%).

Workup

  1. customThe solvent was removed in vacuo
  2. stirringstirred for 1 hr
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with 10% AcOH (30 mL×2)
  5. customdried

Sources & evidence

ORD record
ord-ad2aa9aa628f4cfb9d2d2dd1d37b525f
Source dataset
uspto-grants-2012_01
Patent number
US08093401B2

Reaction notes

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