Pyridine → 2-ethoxy-6-(N-formyl-N-methylamino-methyl)-3,1-benzoxazin-4-one

HRID 557457Notes

Reaction equation

HRID 557457 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH2:11][N:12]([CH:14]=[O:15])[CH3:13])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].N1C=CC=CC=1.Cl[C:23]([O:25][CH2:26][CH3:27])=O>O>[CH2:26]([O:25][C:23]1[O:5][C:4](=[O:6])[C:3]2[CH:7]=[C:8]([CH2:11][N:12]([CH:14]=[O:15])[CH3:13])[CH:9]=[CH:10][C:2]=2[N:1]=1)[CH3:27]

Participants

5

Reactant 3

HCID 1049PyridineHCID 10928Ethyl chloroformateHCID 580183122-amino-5-(N-formyl-N-methylamino-methyl)benzoic acid

Product 1

HCID 580183142-ethoxy-6-(N-formyl-N-methylamino-methyl)-3,1-benzoxazin-4-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 6.0 g of 2-amino-5-(N-formyl-N-methylamino-methyl)-benzoic acid, there was added 30 mL of pyridine and then 11.1 mL of ethyl chloroformate was dropwise added to the mixture while ice-cooling the same. After the elapse of a night, 20 mL of water was dropwise added to the mixture to separate out a solid material, the solid was then isolated through filtration under reduced pressure and washed with 20 mL of water. Then the solid thus separated was dried under reduced pressure to give 3.97 g of the intended compound as a white solid.

Workup

  1. temperaturecooling the same
  2. customto separate out a solid material
  3. customthe solid was then isolated through filtration under reduced pressure
  4. washwashed with 20 mL of water
  5. customThen the solid thus separated
  6. customwas dried under reduced pressure

Sources & evidence

ORD record
ord-4f2ba2d4773e4bb6860dd8adaa63da5d
Source dataset
uspto-grants-2011_11
Patent number
US08058432B2

Reaction notes

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