Formaldehyde → 7-Bromo-2-methyl-1,2,3,4-tetrahydroisoquinoline

HRID 447531Notes

Reaction equation

HRID 447531 reaction equation
[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][NH:8][CH2:9]2)=[CH:4][CH:3]=1.[CH2:12]=O>C(O)=O>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][N:8]([CH3:12])[CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 712FormaldehydeHCID 107292557-Bromo-1,2,3,4-tetrahydroisoquinoline

Product 1

HCID 534084697-Bromo-2-methyl-1,2,3,4-tetrahydroisoquinolineYield 78%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of 7-bromo-1,2,3,4-tetrahydroisoquinoline (1 g, 4.7 mmol) in formic acid (20 mL) was added formalin (1.2 mL, 15 mmol). The solution was heated to 150° C. for 5 min under microwave irradiation. The solvent was removed in vacuo and the residue was dissolved into ethyl acetate (100 mL), washed with sat. sodium bicarbonate (2×10 mL), brine (10 mL) and dried over MgSO4. Removal of the solvent gave the title compound as a white solid (800 mg, 78%). 1H NMR (400 MHz, CDCl3) δ 7.73 (d, J=8.3 Hz, 1H), 7.70 (s, 1H), 7.50 (d, J=8.0 Hz, 1H), 4.11 (s, 2H), 3.37-3.34 (m, 2H), 3.27-3.24 (m, 2H) 2.95 (s, 3H); MS ESI 225.9, 227.9 [M+H]+, calcd for [C10H12BrN+H]+ 226.0, 228.0.

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved into ethyl acetate (100 mL)
  3. washwashed with sat. sodium bicarbonate (2×10 mL), brine (10 mL)
  4. dry with materialdried over MgSO4
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-26c6a4eddf6f4fffb28747c7c1155aa2
Source dataset
uspto-grants-2013_07
Patent number
US08481525B2

Reaction notes

Loading…