Ammonia → 3-(2-Formylphenyl)benzo[d]isoxazole-6-carboxamide

HRID 475430Notes

Reaction equation

HRID 475430 reaction equation
[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]([OH:20])=O)=[CH:17][C:12]=2[O:11][N:10]=1)=[O:2].C(N1C=CN=C1)([N:23]1C=CN=C1)=O.N>CN1CCCC1=O>[CH:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:13]2[CH:14]=[CH:15][C:16]([C:18]([NH2:23])=[O:20])=[CH:17][C:12]=2[O:11][N:10]=1)=[O:2]

Participants

5

Reactant 3

HCID 222AmmoniaHCID 682631,1'-CarbonyldiimidazoleHCID 867622653-(2-Formylphenyl)benzo[d]isoxazole-6-carboxylic acid2×

Product 1

HCID 866759963-(2-Formylphenyl)benzo[d]isoxazole-6-carboxamideYield 91.6%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 3-(2-formylphenyl)benzo[d]isoxazole-6-carboxylic acid (Compound 6) (60.2 g) in N-methyl-2-pyrrolidinone (600 mL) at room temperature was added in one portion 1,1′-carbonyldiimidazole (40.2 g) and the solution stirred at room temperature under nitrogen for 2 h then poured into specific gravity 0.880 aqueous ammonia solution. The suspension was stirred mechanically at room temperature for 2 h then filtered. The still moist collected solid was triturated in methanol (200 mL) at room temperature then filtered, this material was triturated again with methanol (100 mL) then filtered and dried in vacuo to give the title product (54.92 g).

Workup

  1. stirringThe suspension was stirred mechanically at room temperature for 2 h
  2. filtrationthen filtered
  3. customThe still moist collected solid
  4. customwas triturated in methanol (200 mL) at room temperature
  5. filtrationthen filtered
  6. customthis material was triturated again with methanol (100 mL)
  7. filtrationthen filtered
  8. customdried in vacuo

Sources & evidence

ORD record
ord-370afcd2fd07454c998ff5f82366b1c3
Source dataset
uspto-grants-2014_01
Patent number
US08637551B2

Reaction notes

Loading…