Dimethylformamide → 2-{[N-(4-Methoxyphenyl)glycyl]amino}benzoic acid

HRID 1490313Notes

Reaction equation

HRID 1490313 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].[CH3:15][O:16][C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1.CN(C=O)C.[OH-].[K+]>O>[CH3:15][O:16][C:17]1[CH:23]=[CH:22][C:20]([NH:21][CH2:2][C:3]([NH:5][C:6]2[CH:14]=[CH:13][CH:12]=[CH:11][C:7]=2[C:8]([OH:10])=[O:9])=[O:4])=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 7732P-AnisidineHCID 14797Potassium HydroxideHCID 10611190HCID 10611190, compound

Product 1

HCID 151632392-{[N-(4-Methoxyphenyl)glycyl]amino}benzoic acidYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 2-(N-bromoacetylamino)benzoic acid from Example 79 (8.00 g, 31.0 mmol) , para-methoxyaniline (9.55 g, 77.5 mmol) and DMF (80 mL) was heated to 80° 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 cold water (100 mL) and dried under high vacuum at 45° C. to yield 7.62 g (85%) of the title compound as a white solid; 1H NMR (DMSO-d6) δ 13.5 (broad s, 1H), 12.04 (s, 1H), 8.73 (dd, J=8.4, J=1.0, 1H), 7.93 (dd, J=7.8, J=1.8, 1H), 7.59 (td, J=8.0, J=1.8, 1H), 7.13 (td, J=7.6, J=1.2, 1H), 6.73 (dt, J=8.8, J=2.2, 2H), 6.54 (dt, J=9.2, J=2.4, 2H), 6.2 (broad s, 1H), 3.77 (s, 2H), 3.62 (s, 3H); 13C NMR (DMSO-d6) δ 171.18, 168.95, 151.53, 142.2, 140.58, 134.12, 131.12, 122.62, 119.42, 116.03, 114.57, 113.42, 55.20, 49.76; MS (EI, m/z) 300 (M+).

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 cold water (100 mL)
  6. customdried under high vacuum at 45° C.

Sources & evidence

ORD record
ord-3b3194483601499e866206f2634a7b46
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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