Formic Acid → 6-Methoxy-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-2-carbaldehyde

HRID 1935779Notes

Reaction equation

HRID 1935779 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:7][C:6]2([CH3:14])[CH3:13].[CH:15](O)=[O:16].Cl.CN(C)CCCN=C=NCC>ClCCl.C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH2:9][N:8]([CH:15]=[O:16])[CH2:7][C:6]2([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 284Formic AcidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 122832086-Methoxy-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline2×

Product 1

HCID 225688096-Methoxy-4,4-dimethyl-1,2,3,4-tetrahydroisoquinoline-2-carbaldehydeYield 90%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 6-methoxy-4,4-dimethyl-1,2,3,4-tetrahydro-isoquinoline (Intermediate 18, 3.2 g, 16.7 mmol) in anhydrous dichloromethane (40 mL) was treated with formic acid (1 mL, 26.5 mmol) followed 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (3.9 g, 20.34 mmol) and the resulting solution was stirred at ambient temperature overnight. It was then diluted with chloroform and washed with water (×1) and brine (×1), dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to afford the title compound as pale brown viscous oil (3.26 g, 90%).

Workup

  1. washwashed with water (×1) and brine (×1)
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. customevaporated in vacuo

Sources & evidence

ORD record
ord-244a2bea9cc44c1bb74c4d614946daa4
Source dataset
uspto-grants-2002_05
Patent number
US06387892B1

Reaction notes

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