Methanol → 2-Methyl-6,7,8-trimethoxy-1[4,5,6-triethoxy-7-nitro-3-phthalidyl]-1,2,3,4-tetrahydro-isoquinoline

HRID 1155504Notes

Reaction equation

HRID 1155504 reaction equation
[I-].[CH3:2][N+:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([O:17][CH3:18])[C:7]([O:15][CH3:16])=[C:8]([O:13][CH3:14])[CH:9]=2)[CH:4]=1.[CH2:19]([O:21][C:22]1[C:31]([O:32][CH2:33][CH3:34])=[C:30]([O:35][CH2:36][CH3:37])[C:29]([N+:38]([O-:40])=[O:39])=[C:28]2[C:23]=1[CH2:24][O:25][C:26]2=[O:27])[CH3:20].C(=O)([O-])[O-].[K+].[K+].CO>O>[CH3:2][N:3]1[CH2:12][CH2:11][C:10]2[C:5](=[C:6]([O:17][CH3:18])[C:7]([O:15][CH3:16])=[C:8]([O:13][CH3:14])[CH:9]=2)[CH:4]1[CH:24]1[C:23]2[C:28](=[C:29]([N+:38]([O-:40])=[O:39])[C:30]([O:35][CH2:36][CH3:37])=[C:31]([O:32][CH2:33][CH3:34])[C:22]=2[O:21][CH2:19][CH3:20])[C:26](=[O:27])[O:25]1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 64521774,5,6-Triethoxy-7-nitrophthalideHCID 128990142-Methyl-6,7,8-trimethoxy-3,4-dihydro-isoquinolinium iodide

Product 1

HCID 128009352-Methyl-6,7,8-trimethoxy-1[4,5,6-triethoxy-7-nitro-3-phthalidyl]-1,2,3,4-tetrahydro-isoquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

235 g (0.647 mole) of 2-methyl-6,7,8-trimethoxy-3,4-dihydro-isoquinolinium iodide (described in J. Chem. Soc. 1951, 1150), 201.4 g of 4,5,6-triethoxy-7-nitrophthalide and 107 g of potassium carbonate are added to 1.240 liters of methanol. After stirring for 24 hours at a temperature below the boiling point of the solvent, 730 ml of water is added and the reaction solution is allowed to crystallise. The crystals are collected by filtration, washed with water and dried, providing 270 g of C27H34O10N2.

Workup

  1. additionis added
  2. customto crystallise
  3. filtrationThe crystals are collected by filtration
  4. washwashed with water
  5. customdried
  6. customproviding 270 g of C27H34O10N2

Sources & evidence

ORD record
ord-d0b3c160f2e54b30ab7966eec3e733a8
Source dataset
uspto-grants-1981_11
Patent number
US04302458

Reaction notes

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