HCID 14626124, compound → HCID 14626125, compound

HRID 1638704Notes

Reaction equation

HRID 1638704 reaction equation
[CH2:1]([N:3]([CH2:25][CH3:26])[C:4]([O:6][C:7]1[N:8]=[C:9]([CH3:24])[C:10]2[C:15]([C:16]=1[N+:17]([O-])=O)=[CH:14][C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=2)=[O:5])[CH3:2]>CO.[Pd]>[NH2:17][C:16]1[C:15]2[C:10](=[CH:11][C:12]([O:22][CH3:23])=[C:13]([O:20][CH3:21])[CH:14]=2)[C:9]([CH3:24])=[N:8][C:7]=1[O:6][C:4](=[O:5])[N:3]([CH2:25][CH3:26])[CH2:1][CH3:2]

Participants

4

Reactant 1

HCID 14626124HCID 14626124, compound

Product 1

HCID 14626125HCID 14626125, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A slurry of 3-(diethylcarbamyloxy)-6,7-dimethoxy-1-methyl-4-nitroisoquinoline (500 mg, 1.38 mmol) in methanol (50 mL) was hydrogenated in a Parr hydrogenator over 10% Pd/C (100 mg) for 4 hours. The reaction mixture was filtered through a celite pad, the solids were washed with methanol and the combined filtrate and washings were evaporated to dryness in vacuo to yield a yellow solid residue. One recrystallization from methylene chloride/ether afforded pure title compound (437 mg, 95.3%), mp 206°-207° C. IR (KBr) 3455, 3340, 3220, 1720, 1655, 1495, 1440, 1265, 1160 cm-1 ; NMR (CDCl3): δ 1.25 and 1.30 (two partly superimposed br t, 6H, N(CH2CH3)2 ], 2.67 (s, 3H, 1-CH3), 3.20-3.70 [br m, 4H, N(CH2CH3)2 ], 3.93 (s, 3H, OCH3), 3.98 (s, 3H, OCH3), 6.82 (s, 1H, 5- or 8-H), 6.93 (s, 1H, 5- or 8-H); MS (DCI): 334 (MH)+

Workup

  1. filtrationThe reaction mixture was filtered through a celite pad
  2. washthe solids were washed with methanol
  3. customthe combined filtrate and washings were evaporated to dryness in vacuo
  4. customto yield a yellow solid residue
  5. customOne recrystallization from methylene chloride/ether afforded pure title compound (437 mg, 95.3%), mp 206°-207° C

Sources & evidence

ORD record
ord-2587a5010cff4fa0a1e9e30e9d5520d4
Source dataset
uspto-grants-1989_11
Patent number
US04880817

Reaction notes

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