Anthranilic Acid → HCID 103821981, compound

HRID 523206Notes

Reaction equation

HRID 523206 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.S(Cl)(Cl)=O.[Br:15][C:16]1[C:17]([CH3:23])=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[CH:7][C:3]=1[C:4]([NH:19][C:18]1[CH:20]=[CH:21][CH:22]=[C:16]([Br:15])[C:17]=1[CH3:23])=[O:6]

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 1235383-Bromo-o-toluidine

Product 1

HCID 103821981HCID 103821981, compoundYield 42.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 2-aminobenzoic acid (5.00 g, 36.5 mmol) and thionyl chloride (8.68 g, 72.9 mmol) in toluene (50 mL) was heated at reflux for 60 min. The mixture was concentrated in vacuo, and the residue was suspended in THF (50 mL), cooled in an ice-water bath and treated with 3-bromo-2-methylaniline (20.35 g, 109 mmol). The resulting suspension was heated at reflux for 2 h. The cooled mixture was treated with 10% aqueous K2CO3 (50 mL), stirred vigorously for 15 min, and extracted with EtOAc. The organic phase was dried and concentrated. The residue was purified by column chromatography on silica gel to give 2-amino-N-(3-bromo-2-methylphenyl)benzamide as a light yellow solid (4.70 g, 42% yield). Mass spectrum m/z 305, 307 (M+H)+. 1H NMR (400 MHz, chloroform-d) δ 7.72 (d, J=7.9 Hz, 1H), 7.67 (br. s., 1H), 7.54 (dd, J=8.3, 1.2 Hz, 1H), 7.48 (dd, J=7.9, 0.9 Hz, 1H), 7.36-7.31 (m, 1H), 7.15 (t, J=8.0 Hz, 1H), 6.81-6.73 (m, 2H), 5.59 (br. s., 2H), 2.45 (s, 3H).

Workup

  1. temperatureat reflux for 60 min
  2. concentrationThe mixture was concentrated in vacuo
  3. temperaturecooled in an ice-water bath
  4. temperatureThe resulting suspension was heated
  5. temperatureat reflux for 2 h
  6. extractionextracted with EtOAc
  7. customThe organic phase was dried
  8. concentrationconcentrated
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-3e5c023c774547368b734b68d1221088
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

Loading…