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

HRID 1155506Notes

Reaction equation

HRID 1155506 reaction equation
[I-].[CH3:2][N+:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][C:7]([O:15][CH3:16])=[C:8]([O:13][CH3:14])[CH:9]=2)[CH:4]=1.[CH2:17]([O:19][C:20]1[C:29]([O:30][CH2:31][CH3:32])=[C:28]([O:33][CH2:34][CH3:35])[C:27]([N+:36]([O-:38])=[O:37])=[C:26]2[C:21]=1[CH2:22][O:23][C:24]2=[O:25])[CH3:18].C(=O)([O-])[O-].[K+].[K+].CO>O>[CH3:2][N:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][C:7]([O:15][CH3:16])=[C:8]([O:13][CH3:14])[CH:9]=2)[CH:4]1[CH:22]1[C:21]2[C:26](=[C:27]([N+:36]([O-:38])=[O:37])[C:28]([O:33][CH2:34][CH3:35])=[C:29]([O:30][CH2:31][CH3:32])[C:20]=2[O:19][CH2:17][CH3:18])[C:24](=[O:25])[O:23]1

Participants

6

Reactant 4

HCID 887MethanolHCID 11430Potassium CarbonateHCID 28269906,7-Dimethoxy-2-methyl-3,4-dihydroisoquinolin-2-ium iodideHCID 64521774,5,6-Triethoxy-7-nitrophthalide

Product 1

HCID 205609802-Methyl-6,7-dimethoxy-1[4,5,6-triethoxy-7-nitro-3-phthalidyl]-1,2,3,4-tetrahydro-isoquinoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

200 g (0.6 mole) of 2-methyl-6,7-dimethoxy-3,4-dihydro-isoquinolinium iodide (prepared in the same manner as the compound of Example A) 186 g of 4,5,6-triethoxy-7-nitrophthalide and 100 g of potassium carbonate are added to 1.5 l of methanol while stirring. The reaction mixture is stirred for 24 hours at a temperature below the boiling point of the solvent, and is then allowed to cool; 900 ml of water is added and the reaction solution is allowed to crystallise. The solution is filtered, rinsed with methanol, and then with water.

Workup

  1. stirringThe reaction mixture is stirred for 24 hours at a temperature below the boiling point of the solvent
  2. temperatureto cool
  3. customto crystallise
  4. filtrationThe solution is filtered
  5. washrinsed with methanol

Sources & evidence

ORD record
ord-bc17c10b4dd148d4aaee83389a8f65d7
Source dataset
uspto-grants-1981_11
Patent number
US04302458

Reaction notes

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