Ammonia → 2-(Dimethylamino)benzamide

HRID 1167348Notes

Reaction equation

HRID 1167348 reaction equation
[CH3:1][N:2]([CH3:13])[C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5](OC)=[O:6].[NH3:14]>CO.O>[CH3:1][N:2]([CH3:13])[C:3]1[CH:12]=[CH:11][CH:10]=[CH:9][C:4]=1[C:5]([NH2:14])=[O:6]

Participants

5

Reactant 2

HCID 222AmmoniaHCID 82336Methyl N,N-dimethylanthranilate

Product 1

HCID 224780682-(Dimethylamino)benzamideYield 5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

A solution of methyl 2-dimethylamino-benzoate (1.79 g, 10 mmol) in 2 M ammonia in methanol (20 mL) was heated at 80° C. in a sealed reaction vessel for 3 d. Upon cooling to room temperature, it was diluted with water. The product was extracted with diethyl ether. The ethereal extracts were washed with brine and dried over anhydrous magnesium sulfate. The solid was then filtered off, and the filtrate was concentrated in vacuo. Purification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel) eluting with 20% ethyl acetate in hexanes yielded 2-dimethylamino-benzamide (85 m g, 5%).

Workup

  1. extractionThe product was extracted with diethyl ether
  2. washThe ethereal extracts were washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationThe solid was then filtered off
  5. concentrationthe filtrate was concentrated in vacuo
  6. customPurification of the residue by flash chromatography (Biotage system, KP-Sil™ 32-63 μm, 60 Å silica gel)
  7. washeluting with 20% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-a1eb19dd8f4340aab936723c11b25a6c
Source dataset
uspto-grants-2003_09
Patent number
US06617346B1

Reaction notes

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