Water → 4-[[2-Methyl-4-oxo-3,4-dihydro-(2H)-1,3-benzoxazine-2-yl]methoxy]nitrobenzene

HRID 427278Notes

Reaction equation

HRID 427278 reaction equation
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].O=[C:12]([CH3:24])[CH2:13][O:14][C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1.N1CCCCC1.O>C1C=CC=CC=1>[CH3:24][C:12]1([CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[NH:10][C:1](=[O:9])[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[O:4]1

Participants

6

Reactant 4

HCID 962Water2×HCID 5147SalicylamideHCID 8082PiperidineHCID 3085071-(4-Nitrophenoxy)propan-2-one

Product 1

HCID 183569464-[[2-Methyl-4-oxo-3,4-dihydro-(2H)-1,3-benzoxazine-2-yl]methoxy]nitrobenzeneYield 86%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a stirred mixture of salicylamide (6.85 g, 50 mmol) and 4-[2-oxo-propoxy]nitrobenzene (9.75 g, 50 mmol) in benzene (500 mL) was added piperidine (0.52 mL, 5 mmol). The reaction mixture was immersed in a pre-heated oil bath (˜100° C.) and refluxed for 10 h with continuous removal of water using Dean-Stark water separator. The reaction mixture was cooled to room temperature End the precipitated brown coloured solid was filtered, washed with benzene and dried to afford the title compound (13.5 g, 86%).

Workup

  1. customThe reaction mixture was immersed in a pre-heated oil bath
  2. filtrationwas filtered
  3. washwashed with benzene
  4. customdried

Sources & evidence

ORD record
ord-3d08c324cdf244e9b7acf322362868dc
Source dataset
uspto-grants-2001_11
Patent number
US06313113B1

Reaction notes

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