HCID 18975680, compound → HCID 18975651, compound

HRID 2393123Notes

Reaction equation

HRID 2393123 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH3:22])[CH:10]2[C:13]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:15][CH2:14]2)=[CH:5][C:4]=1[CH3:23]>Br.C(O)(=O)C>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH2:8][N:9]([CH3:22])[CH:10]2[C:13]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=3)[CH2:14][CH2:15]2)=[CH:5][C:4]=1[CH3:23]

Participants

4

Reactant 1

HCID 18975680HCID 18975680, compound

Product 1

HCID 18975651HCID 18975651, compoundYield 44.9%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 260Hydrogen BromideSolvent

Procedure

A solution of 7-methoxy-2,6-dimethyl-1-[1-(2-pyridyl)cyclopropyl]-1,2,3,4-tetrahydroisoquinoline (0.7 g) in 48% hydrobromic acid (10 ml) and glacial acetic acid (10 ml) was heated under reflux under nitrogen for 5 hours. The mixture was cooled to ambient temperature, and concentrated in vacuo. Water (50 ml) was added and the solution basified with aqueous sodium hydroxide solution (2N) until the solution had pH 8. The product was extracted with ether (100 ml) and ethyl acetate (200 ml), and the combined organic fractions were washed with water (100 ml). The organic layer was dried over sodium sulphate and the solvents removed in vacuo to yield a brown solid which was triturated with ether to yield 7-hydroxy-2,6-dimethyl-1-[1-(2-pyridyl)cyclopropyl]-1,2,3,4-tetrahydroisoquinoline (0.3 g) as a solid, mp 218° C. (Dec).

Workup

  1. temperatureunder reflux under nitrogen for 5 hours
  2. concentrationconcentrated in vacuo
  3. additionWater (50 ml) was added
  4. extractionThe product was extracted with ether (100 ml) and ethyl acetate (200 ml)
  5. washthe combined organic fractions were washed with water (100 ml)
  6. dry with materialThe organic layer was dried over sodium sulphate
  7. customthe solvents removed in vacuo
  8. customto yield a brown solid which
  9. customwas triturated with ether

Sources & evidence

ORD record
ord-475e13aa61a34eaca0bc4bd292f9e2fd
Source dataset
uspto-grants-1998_09
Patent number
US05804586

Reaction notes

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