Isatoic Anhydride → HCID 16769039, compound

HRID 1846316Notes

Reaction equation

HRID 1846316 reaction equation
[C:1]12[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[NH:6]C(=O)[O:4][C:2]2=O.[O:13]1[CH2:18][CH2:17][N:16]([C:19]2[CH:25]=[CH:24][C:22]([NH2:23])=[CH:21][CH:20]=2)[CH2:15][CH2:14]1>CN(C=O)C.[Cl-].[Li+]>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:23][C:22]1[CH:21]=[CH:20][C:19]([N:16]2[CH2:17][CH2:18][O:13][CH2:14][CH2:15]2)=[CH:25][CH:24]=1)=[O:4]

Participants

5

Reactant 2

HCID 8359Isatoic AnhydrideHCID 75655Benzenamine, 4-(4-morpholinyl)-

Product 1

HCID 16769039HCID 16769039, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 433294Lithium ChlorideSolvent

Conditions

Temperature
115 °C

Procedure

Isatoic anhydride (1.63 g, 10 mmol) was dissolved in DMF (40 mL) and added to 4-morpholinoaniline (1.78 g, 10 mmol). The reaction mixture was heated to 115° C. for 2.5 h. It was then cooled to room temperature, diluted with 5% lithium chloride solution (120 mL), and extracted with ethyl acetate (2×200 mL). The combined organic layers were washed with water (100 mL), 10% aqueous sodium hydroxide (100 mL), and water (100 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated to give 2-amino-N-(4-morpholinophenyl)benzamide as a gray solid. Yield 1.71 g (57%).

Workup

  1. temperatureIt was then cooled to room temperature
  2. extractionextracted with ethyl acetate (2×200 mL)
  3. washThe combined organic layers were washed with water (100 mL), 10% aqueous sodium hydroxide (100 mL), and water (100 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8d8b356283014d62bc06f7a298049238
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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