2-Aminophenol → 2-(3-bromopropyl)-2H-1,4-benzoxazine-3(4H)-one

HRID 2259572Notes

Reaction equation

HRID 2259572 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[OH:8].Br[CH:10]([CH2:15][CH2:16][CH2:17][Br:18])[C:11](OC)=[O:12].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.C(OCC)C>[Br:18][CH2:17][CH2:16][CH2:15][CH:10]1[C:11](=[O:12])[NH:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=2[O:8]1

Participants

6

Reactant 3

HCID 58012-AminophenolHCID 11430Potassium CarbonateHCID 10912698Methyl 2,5-dibromopentanoate

Product 1

HCID 143046582-(3-bromopropyl)-2H-1,4-benzoxazine-3(4H)-oneYield 20.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolvent

Procedure

24 g of 2-aminophenol, 55 g of methyl 2,5-dibromovalerate and 30 g of potassium carbonate were heated to reflux for 5 hours in 250 ml of acetone. For work-up, the reaction mixture was diluted with 250 ml of diethyl ether, washed with 200 ml of water and acidified to pH=1 using 12N hydrochloric acid solution. The organic phase was separated, washed twice with 100 ml of water each time, dried and evaporated. The residue was crystallized from methanol. 11 g of 2-(3-bromopropyl)-2H-1,4-benzoxazin-3(4H)one were obtained.

Workup

  1. washwashed with 200 ml of water
  2. customThe organic phase was separated
  3. washwashed twice with 100 ml of water each time
  4. customdried
  5. customevaporated
  6. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-2becd2a960734871baacef005f50af07
Source dataset
uspto-grants-1995_12
Patent number
US05474988

Reaction notes

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