Triethylamine → 4-methyl-2H-isoquinolin-1-one

HRID 346921Notes

Reaction equation

HRID 346921 reaction equation
[C:1]1([C:7]([CH3:12])=[CH:8]C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=[O:20])C=CC=CC=1.C([N:32]([CH2:35]C)CC)C>C1C=CC=CC=1>[CH3:12][C:7]1[C:1]2[C:2](=[CH:3][CH:4]=[CH:5][CH:6]=2)[C:35](=[O:20])[NH:32][CH:8]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 709803-Phenylbut-2-enoic acidHCID 199401P,P-Diphenylphosphinic azide

Product 1

HCID 126952994-methyl-2H-isoquinolin-1-oneYield 63%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-phenyl-but-2-enoic acid (16.2 g), diphenylphosphoryl azide (27.5 g), and triethylamine (10.1 g) in benzene (100 mL) was stirred for 1 h. After filtration through a silica gel plug washing with benzene and concentration, the residue was dissolved in diphenylmethane (80 mL) and refluxed for 3 h. After cooling to rt, solids were collected through a plug washing with benzene and dried to give 10 g (63%) of the desired 4-methyl-2H-isoquinolin-1-one as a solid. 1H NMR (400 MHz, CD3OD) δ ppm 2.30 (s, 3H), 7.00 (s, 1H), 7.54 (m, 1H), 7.77 (m, 2H), 8.33 (d, J=7.34 Hz, 1H).

Workup

  1. filtrationAfter filtration through a silica gel plug
  2. washwashing with benzene and concentration
  3. dissolutionthe residue was dissolved in diphenylmethane (80 mL)
  4. temperaturerefluxed for 3 h
  5. customsolids were collected through a plug
  6. washwashing with benzene
  7. customdried

Sources & evidence

ORD record
ord-262bf12fe32f4dc986a1c8a04682dab4
Source dataset
uspto-grants-2007_02
Patent number
US07173004B2

Reaction notes

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