Ammonia → Methyl 5-(6-bromo-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate

HRID 927263Notes

Reaction equation

HRID 927263 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=O)[O:7][C:6]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:5]2.CO.[NH3:23]>>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:7])[NH:23][C:6]([CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][CH3:20])=[O:18])=[CH:5]2

Participants

4

Reactant 3

HCID 222AmmoniaHCID 887MethanolHCID 90095220methyl 5-(6-bromo-1-oxo-1H-isochromen-3-yl)pentanoate

Product 1

HCID 118558135Methyl 5-(6-bromo-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate

Procedure

A mixture of methyl 5-(6-bromo-1-oxo-1H-isochromen-3-yl)pentanoate (1.5 g, 4.42 mmol) in 7 N ammonia in MeOH (63.2 ml, 442 mmol, 100.0 equiv.) was left standing at room temperature overnight. The mixture was concentrated, diluted with EtOAc, and added 1 N HCl until pH 4. The mixture was vigorously stirred for 10 min, extracted with EtOAc (2×20 mL), washed with brine, dried over Na2SO4, filtered and evaporated to dryness to yield 1.26 g of methyl 5-(6-bromo-1-oxo-1,2-dihydroisoquinolin-3-yl)pentanoate which was used as such without any further purification.

Workup

  1. waitwas left
  2. concentrationThe mixture was concentrated
  3. additiondiluted with EtOAc
  4. additionadded 1 N HCl until pH 4
  5. extractionextracted with EtOAc (2×20 mL)
  6. washwashed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-17387fd60a5a4cf29e2e4ed817f2ac1a
Source dataset
uspto-grants-2016_03
Patent number
US09290454B2

Reaction notes

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