1,2,3,4-Tetrahydroisoquinoline → HCID 67197253, compound

HRID 2100216Notes

Reaction equation

HRID 2100216 reaction equation
[N+]([C:4]1[CH:11]=[CH:10][CH:9]=[C:6]([C:7]#[N:8])[C:5]=1[C:12]#[N:13])([O-])=O.C(=O)([O-])[O-].[K+].[K+].[CH2:20]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][NH:21]1>O>[CH:20]1([C:4]2[CH:11]=[CH:10][CH:9]=[C:6]([C:7]#[N:8])[C:5]=2[C:12]#[N:13])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH2:23][CH2:22][NH:21]1

Participants

5

Reactant 3

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 11430Potassium CarbonateHCID 1626521,2-Benzenedicarbonitrile, 3-nitro-

Product 1

HCID 67197253HCID 67197253, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
170 °C

Procedure

A mixture of 3-nitrophthalonitrile (2.04 g, 11.8 mmol), freshly dried potassium carbonate (6.0 g, 42 mmol) and 1,2,3,4-tetrahydroisoquinoline (16.5 mL) was heated at 170° C. for 4 h. The reaction mixture was poured into water (250 mL) and extracted with dichloromethane (2×200 mL); the combined organic layers were washed with hydrochloric acid (1 M, 2×200 mL), dried (Na2SO4) and the solvent removed. The product was purified by recrystallisation from methanol to give 9 as a beige powder (906 mg, 30%)

Workup

  1. extractionextracted with dichloromethane (2×200 mL)
  2. washthe combined organic layers were washed with hydrochloric acid (1 M, 2×200 mL)
  3. dry with materialdried (Na2SO4)
  4. customthe solvent removed
  5. customThe product was purified by recrystallisation from methanol

Sources & evidence

ORD record
ord-6c4fbc283169460e9c4b5e90758a8f89
Source dataset
uspto-grants-2009_08
Patent number
US07572327B2

Reaction notes

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