Anthranilic Acid → 2-Propanamidobenzoic acid

HRID 1007158Notes

Reaction equation

HRID 1007158 reaction equation
[C:1]([OH:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].[C:11](Cl)(=[O:14])[CH2:12][CH3:13].O.O.CN(C=O)C>CN(C=O)C>[C:11]([NH:4][C:3]1[CH:5]=[CH:6][CH:7]=[CH:8][C:2]=1[C:1]([OH:10])=[O:9])(=[O:14])[CH2:12][CH3:13]

Participants

6

Reactant 4

HCID 227Anthranilic AcidHCID 962WaterHCID 62324Propionyl chlorideHCID 21962138N,N-Dimethylformamide--water (1/1)

Product 1

HCID 32646742-Propanamidobenzoic acidYield 67.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a room temperature solution of 50.22 g anthranilic acid (I) (370 mmol, 1.00 equiv) dissolved in 200 mL dry DMF was added 35.0 mL propionyl chloride (400 mmol, 1.10 equiv) dropwise by addition funnel over 1.5 h. The addition rate was slow enough to maintain internal temperature of the reaction below 38° C. Upon completed addition of the acid chloride, the heterogeneous reaction mixture was stirred for 2.5 h at ambient temperature and then poured into 1600 mL water. The resulting water/DMF mixture, with white precipitate, was stirred vigorously at ambient temperature for one h, after which time the solid was collected by vacuum filtration, rinsing the solid with cold water (2×100 mL). The product was dried in vacuo over phosphorous pentoxide overnight affording 48.04 g of a white solid. m.p. 120.1° C. 1H NMR (CDCl3) δ1.30 (t, 3H, J=7.4 Hz), 2.52 (q, 2H, J=7.4 Hz), 7.12 (t, 1H, J=7.2 Hz), 7.60 (t, 1H, J=7.1 Hz), 8.13 (d, 1H, J=6.3 Hz), 8.76 (d, 1H, J=7.8 Hz) ppm. MS (ESI−) 192.1 [M−H]−.

Workup

  1. additiondropwise by addition funnel over 1.5 h
  2. temperatureto maintain internal
  3. customtemperature of the reaction below 38° C
  4. filtrationafter which time the solid was collected by vacuum filtration
  5. washrinsing the solid with cold water (2×100 mL)
  6. dry with materialThe product was dried in vacuo over phosphorous pentoxide overnight

Sources & evidence

ORD record
ord-d668305c2b1d4a30ab009d4027386e0e
Source dataset
uspto-grants-2004_09
Patent number
US06794379B2

Reaction notes

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