Sodium Hydroxide → 6-Methoxy-1,2,3,4-tetrahydroisoquinoline

HRID 1503880Notes

Reaction equation

HRID 1503880 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[C:15](=O)[NH:14][CH2:13][CH2:12]2.[OH-].[Na+]>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH2:15][NH:14][CH2:13][CH2:12]2

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 106073926-methoxy-3,4-dihydroisoquinolin-1(2H)-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 393566-Methoxy-1,2,3,4-tetrahydroisoquinoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

To a suspension of lithium aluminum hydride (10 g, 46 mmol) in tetrahydrofuran (100 mL) at 0° C. under nitrogen was added slowly a solution of the product of Example 53B (4.1 g, 23 mmol) in tetrahydrofuran (50 mL) over 0.5 hours and the mixture was heated at 70° C. for 2 hours. After cooling to 0° C., 15% sodium hydroxide (4.9 mL) was added slowly and the mixture was filtered and washed with ethyl acetate (50 mL). The filtrate was concentrated to give the crude title compound. MS: 164 (M+H+).

Workup

  1. temperatureAfter cooling to 0° C.
  2. filtrationthe mixture was filtered
  3. washwashed with ethyl acetate (50 mL)
  4. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-0948949eebdc4d05b25588e2e8827b0b
Source dataset
uspto-grants-2015_12
Patent number
US09212192B2

Reaction notes

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