Trifluoroacetic acid → 2-methyl-4-(3,4,5-trimethoxyphenyl)-8-isopropoxy-7-methoxy-1,4-dihydro-3(2H)-isoquinolinone

HRID 1666312Notes

Reaction equation

HRID 1666312 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:13](OC(=O)C)[C:14]([N:16]([CH3:30])[CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:19]=2[O:26][CH:27]([CH3:29])[CH3:28])=[O:15])[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].FC(F)(F)C(O)=O>ClCCl>[CH3:30][N:16]1[C:14](=[O:15])[CH:13]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)[C:23]2[C:18](=[C:19]([O:26][CH:27]([CH3:29])[CH3:28])[C:20]([O:24][CH3:25])=[CH:21][CH:22]=2)[CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 670818692-(3,4,5-trimethoxyphenyl)-2-acetoxy-N-methyl-N-(2-isopropoxy-3-methoxybenzyl)acetamide

Product 1

HCID 670818192-methyl-4-(3,4,5-trimethoxyphenyl)-8-isopropoxy-7-methoxy-1,4-dihydro-3(2H)-isoquinolinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of the amide from step 2 above (6.2 g) in dichloromethane (60 ml) and trifluoroacetic acid (20 ml) was refluxed for 6 hours. The reaction mixture was concentrated to dryness and the residue was crystallized from methanol, giving 2-methyl-4-(3,4,5-trimethoxyphenyl)-8-isopropoxy-7-methoxy-1,4-dihydro-3(2H)-isoquinolinone (4.8 g), m.p. 128-129° C.

Workup

  1. concentrationThe reaction mixture was concentrated to dryness
  2. customthe residue was crystallized from methanol

Sources & evidence

ORD record
ord-10c6c26fdcac4290a295e8802e1c3c83
Source dataset
uspto-grants-2011_10
Patent number
US08044067B2

Reaction notes

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