Pyridine → HCID 67401999, compound

HRID 906112Notes

Reaction equation

HRID 906112 reaction equation
[C:1](Cl)(=[O:3])[CH3:2].[NH2:5][C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][C:18]=1[C:19]([NH2:21])=[O:20])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].N1C=CC=CC=1>O1CCCC1>[C:1]([NH:5][C:6]1[CH:7]=[C:8]([CH:16]=[CH:17][C:18]=1[C:19]([NH2:21])=[O:20])[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 6367Acetyl chlorideHCID 22402069HCID 22402069, compound

Product 1

HCID 67401999HCID 67401999, compoundYield 157.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Acetyl chloride (50 uL, 0.32 mmol) was added to a solution of 1,1-dimethylethyl 3-amino-4-(aminocarbonyl)benzoate (126 mg, 0.53 mmol) and pyridine (52 uL, 0.64 mmol) in tetrahydrofuran (3 mL) at 0° C., and the resulting mixture was stirred at 0° C. for one hour. The mixture was quenched with ice-water (10 mL) and extracted ethyl acetate (3×10 mL). The combined extract was washed with 15 mL, each of 5% aqueous citric acid, saturated aqueous sodium bicarbonate, and brine solutions then dried over sodium sulfate, filtered and concentrated to give the 1,1-dimethylethyl 3-(acetylamino)-4-(aminocarbonyl)benzoate (140 mg, 94% yield). MS (EI) for C14H18N2O4: 279 (MH+).

Workup

  1. customThe mixture was quenched with ice-water (10 mL)
  2. extractionextracted ethyl acetate (3×10 mL)
  3. extractionThe combined extract
  4. washwas washed with 15 mL
  5. dry with materialeach of 5% aqueous citric acid, saturated aqueous sodium bicarbonate, and brine solutions then dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ea7203cefbb347dd96d45340c6b6b8c2
Source dataset
uspto-grants-2011_09
Patent number
US08012956B2

Reaction notes

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