Methanol → 8-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-one

HRID 511331Notes

Reaction equation

HRID 511331 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([CH3:13])[CH:8]=[CH:7]2.CO>C(O)(=O)C.C(Cl)Cl.CCOC(C)=O.O=[Pt]=O>[NH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:10](=[O:12])[N:9]([CH3:13])[CH2:8][CH2:7]2

Participants

7

Reactant 2

HCID 887MethanolHCID 67254528HCID 67254528, compound2×

Product 1

HCID 162026268-amino-2-methyl-3,4-dihydroisoquinolin-1(2H)-oneYield 26.3%

Reagents, catalysts & solvents 4

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 8-amino-2-methylisoquinolin-1(2H)-one (Compound 131A, 100 mg, 0.54 mmol) in acetic acid (10 mL) was hydrogenated over PtO2 (24 mg) at room temperature for 16 h. TLC (5% MeOH in CH2Cl2) showed the reaction was complete. The catalyst was filtered off through Celite and the filtrate was evaporated to dryness to give a residue, which was dissolved in EtOAc (20 mL), washed with aq. sat. NaHCO3 (20 mL), water (10 mL), dried and evaporated, residue was purified by column chromatography on silica gel (5% MeOH in CH2Cl2) to give the desired product (25 mg, 25%). 1H NMR (CDCl3, 300 MHz): δ=2.96 (t, J=6.6 Hz, 2 H), 2.98 (s, 3 H), 3.55 (t, J=6.9 Hz, 2 H), 6.18 (br, 2 H), 6.45 (d, J=6.9 Hz, 1 H), 6.58 (d, J=7.5 Hz, 1 H), 7.15 (t, J=7.5 Hz, 1 H).

Workup

  1. filtrationThe catalyst was filtered off through Celite
  2. customthe filtrate was evaporated to dryness
  3. customto give a residue, which
  4. washwashed with aq. sat. NaHCO3 (20 mL), water (10 mL)
  5. customdried
  6. customevaporated
  7. customresidue was purified by column chromatography on silica gel (5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-063bffbbf3e1428cbb91cfa3d7e0adff
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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