Isatoic Anhydride → HCID 67459390, compound

HRID 1846360Notes

Reaction equation

HRID 1846360 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.[CH:13]1([C:16]2[CH:22]=[CH:21][C:19]([NH2:20])=[CH:18][CH:17]=2)[CH2:15][CH2:14]1>CN(C=O)C>[NH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:1]=1[C:2]([NH:20][C:19]1[CH:21]=[CH:22][C:16]([CH:13]2[CH2:15][CH2:14]2)=[CH:17][CH:18]=1)=[O:4]

Participants

4

Reactant 2

HCID 8359Isatoic AnhydrideHCID 122539274-Cyclopropylaniline

Product 1

HCID 67459390HCID 67459390, compoundYield 56.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
135 °C

Procedure

Isatoic anhydride (0.393 g, 2.41 mmol) and 4-cyclopropylaniline (0.320 g, 2.41 mmol) were dissolved in DMF (5 mL) and heated at 135° C. for 5 hours. The reaction mixture was concentrated, and purified by silica gel chromatography, eluting with 30% ethyl acetate/heptane to 100% ethyl acetate, to afford 2-amino-N-(4-cyclopropylphenyl)benzamide as a white solid (0.342 g, 56%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompurified by silica gel chromatography
  3. washeluting with 30% ethyl acetate/heptane to 100% ethyl acetate

Sources & evidence

ORD record
ord-70b8ea573fa84c86b7215fd147edc8d9
Source dataset
uspto-grants-2015_02
Patent number
US08952021B2

Reaction notes

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