Aniline → HCID 67598504, compound

HRID 582683Notes

Reaction equation

HRID 582683 reaction equation
[Cl:1][C:2]1[C:3]([NH:11][C:12](=[O:15])[CH2:13]Br)=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6].[NH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.CN(C=O)C.[OH-].[K+]>O>[Cl:1][C:2]1[C:3]([N:11]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:12](=[O:15])[CH3:13])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=[O:6]

Participants

6

Reactant 4

HCID 6115AnilineHCID 6228DimethylformamideHCID 14797Potassium HydroxideHCID 189292153-Chloro-2-(bromoacetamido)benzoic Acid

Product 1

HCID 67598504HCID 67598504, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 3-chloro-2-(bromoacetamido) benzoic acid from Example 39 (4.6 g, 15.7 mmol), aniline (3.58 mL, 39.3 mmol) and DMF (45 mL) was heated to 80° C. for 8 h. The mixture was cooled, poured over H2O (400 mL) and 5% KOH (125 mL) and washed with CH2Cl2 (3×125 mL). The aqueous layer was acidified to pH 2 with 2 N HCl, cooled below room temperature and filtered. The filter cake was rinsed with cold water (50 mL) and dried under high vacuum at 45° C. to yield 3.19 g (67%) of the title compound as a tan solid; 1H NMR (DMSO-d6) δ 13.1 (broad s, 1H), 9.85 (s, 1H), 7.74 (d, J=7.6, 1H), 7.71 (d, J=8.0, 1H), 7.35 (t, J=7.6, 1H), 7.10 (t, J=7.6, 2H), 6.65-6.58 (m, 3H), 6.1 (broad s, 1H), 3.82 (s, 2H); 13C NMR (DMSO-d6) δ 169.62, 166.77, 148.33, 133.87, 132.70, 131.53, 130.93, 128.90, 128.82, 127.21, 116.59, 112.57, 47.16; MS (LSIMS, m/z) 305 (M+H+)

Workup

  1. temperatureThe mixture was cooled
  2. washwashed with CH2Cl2 (3×125 mL)
  3. temperaturecooled below room temperature
  4. filtrationfiltered
  5. washThe filter cake was rinsed with cold water (50 mL)
  6. customdried under high vacuum at 45° C.

Sources & evidence

ORD record
ord-21fd971d1bf94fd2b9bf4e0211636f97
Source dataset
uspto-grants-1999_07
Patent number
US05925647

Reaction notes

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