Dimethylformamide → HCID 10684750, compound

HRID 1490318Notes

Reaction equation

HRID 1490318 reaction equation
Br[CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])=[O:4].[F:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18].CN(C=O)C.[OH-].[K+]>O>[F:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH:18][CH2:2][C:3]([NH:5][C:6]1[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=1[C:8]([OH:10])=[O:9])=[O:4]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 95842-FluoroanilineHCID 14797Potassium HydroxideHCID 10611190HCID 10611190, compound

Product 1

HCID 10684750HCID 10684750, compoundYield 85.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(N-bromoacetylamino)benzoic acid from Example 79 (8.00 g, 31.0 mmol), ortho-fluoroaniline (7.48 mL, 77.5 mmol) and DMF (80 mL) was heated to 75° C. for 8 h. The mixture was cooled, poured over H2O (1 L) and 5% KOH (300 mL) and washed with CH2Cl2 (3×300 mL). The aqueous layer was acidified to pH 2 with 2N HCl, cooled below room temperature and filtered. The filter cake was rinsed with water (60 mL) and dried under high vacuum at 45° C. to yield 7.62 g (85%) of the title compound as an off-white solid; 1H NMR (DMSO-d6) δ 13.54 (broad s, 1H), 12.01 (s, 1H), 8.72 (d, J=8.4, 1H), 7.93 (dd, J=8, J=1.4, 1H), 7.59 (td, J=7.2, J=1.6, 1H), 7.13 (t, J=7.6, 1H), 7.05 (dd, J=11.6, J=8.0, 1H), 6.94 (t, J=7.6, 1H), 6.58 (m, 2H), 6.37 (broad s, 1H), 3.90 (d, J=5.6, 2H); 13C NMR (DMSO-d6) δ 170.30, 169.19, 151.02 (J=238.1), 140.56, 136.00 (J=11.3), 134.20, 131.12, 124.77 (J=3.1), 122.71, 119.35, 116.80 (J=6.8), 114.52 (J=18.2), 111.81 (J=3.1), 48.23.

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with CH2Cl2 (3×300 mL)
  3. temperaturecooled below room temperature
  4. filtrationfiltered
  5. washThe filter cake was rinsed with water (60 mL)
  6. customdried under high vacuum at 45° C.

Sources & evidence

ORD record
ord-30f068da564c47b3a336566b482c624e
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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