Trifluoroacetic acid → N-(1,2,3,4-Tetrahydroisoquinolin-5-yl)-5-chloro-2,4-dimethoxybenzamide

HRID 1872725Notes

Reaction equation

HRID 1872725 reaction equation
[Cl:1][C:2]1[C:3]([O:30][CH3:31])=[CH:4][C:5]([O:28][CH3:29])=[C:6]([CH:27]=1)[C:7]([NH:9][C:10]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:11]=1[CH2:12][CH2:13][N:14](C(OC(C)(C)C)=O)[CH2:15]2)=[O:8].FC(F)(F)C(O)=O.C(=O)(O)[O-].[Na+]>ClCCl>[CH2:15]1[C:16]2[C:11](=[C:10]([NH:9][C:7](=[O:8])[C:6]3[CH:27]=[C:2]([Cl:1])[C:3]([O:30][CH3:31])=[CH:4][C:5]=3[O:28][CH3:29])[CH:19]=[CH:18][CH:17]=2)[CH2:12][CH2:13][NH:14]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 186873951,1-Dimethylethyl 5-[(5-chloro-2,4-dimethoxybenzoyl)amino]-3,4-dihydro-2(1H)-isoquinolinecarboxylate

Product 1

HCID 18687356N-(1,2,3,4-Tetrahydroisoquinolin-5-yl)-5-chloro-2,4-dimethoxybenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-chloro-2,4-dimethoxy-N-[2-(tert-butoxycarbonyl)-1,2,3,4-tetrahydroisoquinolin-5-yl]benzamide (1 g) in dichloromethane (30 ml) at 0° C. was added trifluoracetic acid (3 ml). The mixture was then stirred at room temperature for 3h before pouring into saturated aqueous sodium bicarbonate (100 ml) and extracting with dichloromethane. The organic phase was dried over sodium sulfate and concentrated in vacuo to afford the title compound as an off white solid (700 mg).

Workup

  1. extractionextracting with dichloromethane
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9ecb945c40ac4551ad50d19142478f3e
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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