1,2,3,4-Tetrahydroisoquinoline → Isoquinoline, 1,2,3,4-tetrahydro-2-(3-nitro-2-pyridinyl)-

HRID 2307275Notes

Reaction equation

HRID 2307275 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.[CH2:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH2:13][NH:12]1>C(O)(C)C>[N+:8]([C:5]1[C:4]([N:12]2[CH2:13][CH2:14][C:15]3[C:20](=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH2:11]2)=[N:3][CH:2]=[CH:7][CH:6]=1)([O-:10])=[O:9]

Participants

4

Reactant 2

HCID 70461,2,3,4-TetrahydroisoquinolineHCID 783082-Chloro-5-nitropyridine

Product 1

HCID 9196247Isoquinoline, 1,2,3,4-tetrahydro-2-(3-nitro-2-pyridinyl)-

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 2-chloro-5-nitro-pyridine (1.58 g, 10 mmol) in isopropanol (30 ml) was treated at rt with 1,2,3,4-tetrahydro-isoquinoline (2.6 g, 20 mmol). The resulting mixture was stirred for 3 hr. The precipitate was filtered, partitioned (AcOEt/H2O) and the organic phase dried (Na2SO4). After evaporation of the solvent the title compound was obtained as a yellow solid mass (1.4 g, 55%), MS: m/e=256 (M+H+).

Workup

  1. filtrationThe precipitate was filtered
  2. custompartitioned (AcOEt/H2O)
  3. dry with materialthe organic phase dried (Na2SO4)
  4. customAfter evaporation of the solvent the title compound
  5. customwas obtained as a yellow solid mass (1.4 g, 55%), MS

Sources & evidence

ORD record
ord-ef8bcb5f8ba04e21bef742440de7daca
Source dataset
uspto-grants-2004_12
Patent number
US06831087B2

Reaction notes

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