Ethyl 3-aminobenzoate → HCID 67827973, compound

HRID 1708563Notes

Reaction equation

HRID 1708563 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7]CC)=[O:6].[Cl:13][C:14]1[CH:19]=[CH:18][N:17]=[CH:16][C:15]=1[N+:20]([O-:22])=[O:21]>C(O)C>[ClH:13].[N+:20]([C:15]1[CH:16]=[N:17][CH:18]=[CH:19][C:14]=1[NH:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([OH:7])=[O:6])([O-:22])=[O:21]

Participants

4

Reactant 2

HCID 11400Ethyl 3-aminobenzoateHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 67827973HCID 67827973, compoundYield 70.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 3-aminobenzoate (3.3 g, 20 mmol) and 4-chloro-3-nitropyridine (3.17 g, 20 mmol) in ethanol (150 ml) was stirred at room temperature for 16 hours and then cooled in an ice-bath. The resulting precipitate was collected, washed with ice-cold ethanol and dried to give ethyl (3-(3-nitro-4-pyridylamino)benzoate hydrochloride (4.17 g) as a yellow crystalline solid, m.p. 201°-204° C. Found: C,5.2; H,4.4; N,12.9. C14H13N3O4. HCl requires C,51.9; H,4.3; N,13.0%. The mother liquors were evaporated and the residue recrystallised from ethanol to give a further 1.2 g of product.

Workup

  1. temperaturecooled in an ice-bath
  2. customThe resulting precipitate was collected
  3. washwashed with ice-cold ethanol
  4. customdried

Sources & evidence

ORD record
ord-87f14c00166e401789798561e582c960
Source dataset
uspto-grants-1994_10
Patent number
US05358953

Reaction notes

Loading…