Sodium Carbonate → HCID 67215375, compound

HRID 2421137Notes

Reaction equation

HRID 2421137 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][N:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:23][C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25]=1[C:35]([NH:37][NH2:38])=O.P(Cl)(Cl)(Cl)=O.C(=O)([O-])[O-].[Na+].[Na+]>ClC1C=CC=CC=1.C(OCC)(=O)C>[CH3:23][C:24]1[O:28][N:27]=[C:26]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[C:25]=1[C:35]1[O:8][C:6]([C:5]2[CH:9]=[CH:10][C:2]([NH2:1])=[N:3][CH:4]=2)=[N:38][N:37]=1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 184966-Aminonicotinic acidHCID 24813Phosphorus oxychlorideHCID 682631,1'-CarbonyldiimidazoleHCID 7279245-Methyl-3-phenyl-4-isoxazolecarbohydrazide

Product 1

HCID 67215375HCID 67215375, compoundYield 9.2%

Reagents, catalysts & solvents 2

HCID 7964ChlorobenzeneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 6-aminonicotinic acid (191 mg, 1.38 mmol) in chlorobenzene (2 mL) was added 1,1′-carbonyl-diimidazole (224 mg, 1.38 mmol) and the resulting mixture stirred for 2 h at 90° C. After the suspension was cooled to ambient temperature 5-methyl-3-phenyl-isoxazole-4-carboxylic acid hydrazide (200 mg, 0.92 mmol) was added and stirred for 1 h at 90° C. After the reaction mixture was cooled to ambient temperature phosphorous oxychloride (0.84 mL, 9.20 mmol) was added and stirring was continued for 4 h at 90° C. The cooled reaction mixture was poured carefully onto a mixture of ethyl acetate (20 mL) and aqueous sodium carbonate (saturated, 20 mL) and was stirred for 1 h at ambient temperature. The aqueous layer was separated and extracted with ethyl acetate (20 mL) and the combined organic layers were washed with aqueous sodium carbonate (saturated). Drying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane:methanol=40:40:20:0 to 0:75:20:5) afforded the title compound (27 mg, 9%) as a white solid. MS: m/e=320.0 [M+H]+.

Workup

  1. additionwas added
  2. stirringstirred for 1 h at 90° C
  3. additionwas added
  4. stirringstirring
  5. waitwas continued for 4 h at 90° C
  6. customThe cooled reaction mixture
  7. stirringwas stirred for 1 h at ambient temperature
  8. customThe aqueous layer was separated
  9. extractionextracted with ethyl acetate (20 mL)
  10. washthe combined organic layers were washed with aqueous sodium carbonate (saturated)
  11. dry with materialDrying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane:methanol=40:40:20:0 to 0:75:20:5)

Sources & evidence

ORD record
ord-168d8c39016b49fba5f3f67e60ea24ee
Source dataset
uspto-grants-2011_06
Patent number
US07956074B2

Reaction notes

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