Water → 5-Bromo-1,2,3,4-tetrahydroisoquinolin-1-one

HRID 387658Notes

Reaction equation

HRID 387658 reaction equation
C[O:2][C:3](=O)[NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[Br:13].P(=O)(O)(O)O.O>C(OCC)(=O)C>[Br:13][C:8]1[CH:9]=[CH:10][CH:11]=[C:12]2[C:7]=1[CH2:6][CH2:5][NH:4][C:3]2=[O:2]

Participants

5

Reactant 3

HCID 962WaterHCID 1004Phosphoric AcidHCID 59401358Methyl[2-(2-bromophenyl)ethyl]carbamate

Product 1

HCID 218654725-Bromo-1,2,3,4-tetrahydroisoquinolin-1-oneYield 8.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1.36 g of methyl[2-(2-bromophenyl)ethyl]carbamate and 5.2 g of phosphoric acid are stirred under an inert atmosphere at a temperature close to 150° C. The reaction mixture is cooled to a temperature close to 20° C., then it is hydrolysed with a mixture of water and ethyl acetate using ultrasound treatment. After decanting, the organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, water, a saturated aqueous solution of sodium chloride, then concentrated using a rotary evaporator under reduced pressure (5 kPa). 0.105 g of 5-bromo-3,4-dihydroisoquinolin-1(2H)-one is obtained in the form of an amorphous beige solid.

Workup

  1. customclose to 150° C
  2. temperatureThe reaction mixture is cooled to a temperature
  3. customclose to 20° C.
  4. customAfter decanting
  5. washthe organic phase is washed with a saturated aqueous solution of sodium hydrogen carbonate, water
  6. concentrationa saturated aqueous solution of sodium chloride, then concentrated
  7. customa rotary evaporator under reduced pressure (5 kPa)

Sources & evidence

ORD record
ord-741e3cf3c5e3446c9e76bcb2c20f8508
Source dataset
uspto-grants-2013_02
Patent number
US08372864B2

Reaction notes

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