Ammonia → 3,4-Dihydro-8-fluoro-2H-1,4-benzoxazine-2-carboxamide

HRID 1184352Notes

Reaction equation

HRID 1184352 reaction equation
[F:1][C:2]1[C:11]2[O:10][CH2:9][CH2:8][NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1.CC[C:14]([O-:16])=O.[NH3:17]>C(O)C>[F:1][C:2]1[C:11]2[O:10][CH:9]([C:14]([NH2:17])=[O:16])[CH2:8][NH:7][C:6]=2[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222Ammonia2×HCID 866648003,4-Dihydro-8-fluoro-2H-1,4-benzoxazine 2-ethyl carboxylate

Product 1

HCID 674804863,4-Dihydro-8-fluoro-2H-1,4-benzoxazine-2-carboxamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 5b (1.1 g, 4.89 mmol) in ethanol (20 mL) an ammonia solution is added (32%, 5 mL). The solution obtained is agitated 14 h at ambient temperature then 10 mL of ammonia are added and the mixture agitated for 48 h. The solution is concentrated under reduced pressure and the residue is dissolved in petroleum ether. The formed precipitate is filtered, washed in petroleum ether and vacuum dried (0.75 g, 78%).

Workup

  1. customThe solution obtained
  2. stirringthe mixture agitated for 48 h
  3. concentrationThe solution is concentrated under reduced pressure
  4. dissolutionthe residue is dissolved in petroleum ether
  5. filtrationThe formed precipitate is filtered
  6. washwashed in petroleum ether
  7. customvacuum dried (0.75 g, 78%)

Sources & evidence

ORD record
ord-32bfdf6a852048eebac9dbfae24d448e
Source dataset
uspto-grants-2014_03
Patent number
US08669250B2

Reaction notes

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