HCID 19610235, compound → HCID 19610221, compound

HRID 1602177Notes

Reaction equation

HRID 1602177 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([C:14]([O:16][CH3:17])=[O:15])[N:9]=[C:10]2[CH3:13])=[CH:5][CH:4]=1.[H][H]>[Pd]>[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH2:7][CH:8]([C:14]([O:16][CH3:17])=[O:15])[NH:9][CH:10]2[CH3:13])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 19610235HCID 19610235, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 19610221HCID 19610221, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 3,4-dihydro-7-methoxy-3-methoxycarbonyl-1-methyl-isoquinoline (2.0 g. 8.57 mmol). obtained from the previous step, in veOH (I 50 mL) was added Pd/C (0.g). The reaction mixture was hydrogenated for 21 hr at 4 atm hydrogen pressure. The catalyst was filtered off and the filtrate was concentrated in vacuo. The oily residue (2 g) was purified by a silica gel column using (1: 1) ethyl acetate/ hexane to yield a yellowish oil (94 %): IR (MIC) U 3340, 2951, 1739, 1616, 1503, 1436, 1290, 1228, 1035 cm-1 ; 1H-NMR (CDCl3, δ): 1.51 (d.J=6.6 Hz, 3H). 2.75 (broad s, 1H), 2.89- 3.03 (m. 2H), 3.72 (dd, J=4.5, 11.1 Hz, 1H). 3.79 (s. 6H), 4.14 (q. J=6.6 Hz, 1H), 6.71- 6.75 (m, 2H), 7.02 (d, J=7.8 Hz, I H): MS showed (M+H) +@ 236; Anal. Calcd for C13Hl7NO3 . HCl: C, 57.46; H, 6.68; N, 5.15; Found: C, 57.42; H, 6.64; N, 5.02.

Workup

  1. customobtained from the previous step, in veOH (I 50 mL)
  2. filtrationThe catalyst was filtered off
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe oily residue (2 g) was purified by a silica gel column

Sources & evidence

ORD record
ord-acf4f931245347769fb7f57e0470bf50
Source dataset
uspto-grants-1999_11
Patent number
US05981521

Reaction notes

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