5-Amino-2-chlorobenzoic acid → HCID 59652729, compound

HRID 1662840Notes

Reaction equation

HRID 1662840 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8].[CH3:12][C:13]1[O:17][N:16]=[C:15]([C:18](Cl)=[O:19])[CH:14]=1>C(Cl)Cl>[CH3:12][C:13]1[O:17][N:16]=[C:15]([C:18]([NH:1][C:2]2[CH:3]=[CH:4][C:5]([Cl:11])=[C:6]([CH:10]=2)[C:7]([OH:9])=[O:8])=[O:19])[CH:14]=1

Participants

4

Reactant 2

HCID 378795-Amino-2-chlorobenzoic acidHCID 27368945-Methylisoxazole-3-carbonyl chloride

Product 1

HCID 59652729HCID 59652729, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-amino-2-chlorobenzoic acid (342 mg, 2.0 mmol) and TEA (1.39 mL, 10 mmol), was added 5-methylisoxazole-3-carbonyl chloride (300 mg, 2.06 mmol) in DCM (5 mL). The reaction mixture was stirred at room temperature for 16 hr, and triturated with aqueous sodium bicarbonate. The organic layer was separated, dried (Na2SO4) and evaporated. The residue on filtered through a silica plug to give the title compound as a cream colored solid (330 mg, 57%).

Workup

  1. customtriturated with aqueous sodium bicarbonate
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. filtrationThe residue on filtered through a silica plug

Sources & evidence

ORD record
ord-7f6ca35a0fb4479bb16f05dc7b0b9625
Source dataset
uspto-grants-2011_10
Patent number
US08030487B2

Reaction notes

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