Acetic Acid → HCID 59680217, compound

HRID 1667023Notes

Reaction equation

HRID 1667023 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8](Cl)=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[OH:20].C([O-])([O-])=O.[Na+].[Na+].CC(O)=O>N1C=CC=CC=1.O>[OH:20][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:14]=1[NH:13][C:8](=[O:9])[C:7]1[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 85024-Nitrobenzoyl chlorideHCID 10340Sodium CarbonateHCID 27624194-Amino-3-hydroxypyridine

Product 1

HCID 59680217HCID 59680217, compoundYield 52%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent2×

Procedure

A solution of p-nitrobenzoyl chloride (4.8 g, 25.7 mmol) in pyridine (50 mL) was added to a solution of 4-amino-3-hydroxypyridine (2.5 g, 22.7 mmol) in pyridine (88 mL) at 10° C. and stirred at room temperature overnight. To the reaction mixture was added Na2CO3 (1.1 g, 10.4 mmol) in water (10 mL) and stirred for 1 hrs. 10% AcOH was added to neutralize the solution. The precipitate was collected by filtration, washed with 10% AcOH and dried to give N-(3-hydroxypyridin-4-yl)-4-nitrobenzamide as a yellow powder (2.27 g, yield: 52%). MS (ESI) calcd. for C12H9N3O4 (m/z): 259, found: 260 [M+H]+.

Workup

  1. stirringstirred for 1 hrs
  2. filtrationThe precipitate was collected by filtration
  3. washwashed with 10% AcOH
  4. customdried

Sources & evidence

ORD record
ord-c2f2e374904c4d0d8ca3d55aaceba32f
Source dataset
uspto-grants-2011_10
Patent number
US08044198B2

Reaction notes

Loading…