Potassium Carbonate → 6-Ethoxycarbonylamino-1-methyl-3,4-dihydroisoquinoline

HRID 1005685Notes

Reaction equation

HRID 1005685 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:8]=1)(=O)[CH3:2].C(=O)([O-])[O-].[K+].[K+]>>[CH2:17]([O:16][C:14]([NH:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[C:1]([CH3:2])=[N:4][CH2:5][CH2:6]2)=[O:15])[CH3:18]

Participants

3

Reactant 2

HCID 11430Potassium CarbonateHCID 22674171N-Acetyl-N-(3-ethoxycarbonylaminophenethyl)amine

Product 1

HCID 226741196-Ethoxycarbonylamino-1-methyl-3,4-dihydroisoquinoline

Procedure

Using 1.0 g of N-acetyl-N-(3-ethoxycarbonylaminophenethyl)amine (Preparation Example 30), cyclization reaction was conducted according to the procedure described in Heterocycles 31(2), 341 (1990). After the completion of the reaction, the reaction mixture was poured onto ice, the mixture was basified with potassium carbonate, and extracted with ethyl acetate. The extract was washed with brine, dried over anhydrous magnesium sulfate and the solvent was evaporated, to give the title compound as brown oil.

Workup

  1. customAfter the completion of the reaction
  2. additionthe reaction mixture was poured onto ice
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated

Sources & evidence

ORD record
ord-ecefc55a51014799b27966792eb14a58
Source dataset
uspto-grants-2004_09
Patent number
US06787534B2

Reaction notes

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