Ammonium Acetate → HCID 69680903, compound

HRID 896247Notes

Reaction equation

HRID 896247 reaction equation
[CH3:1][N:2]1[CH2:11][C:10](=O)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3]1.C([O-])(=O)C.[NH4+].[BH3-]C#[N:20].[Na+]>CO>[NH2:20][CH:10]1[CH:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH2:8]2)[CH2:3][N:2]([CH3:1])[CH2:11]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 106308122-Methyl-2,3-dihydroisoquinolin-4(1H)-one

Product 1

HCID 69680903HCID 69680903, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to Scheme 23, a mixture of 2-methyl-2,3-dihydro-4-(1H)-isoquinolone (630 mg, 3.9 mmol, Nichols, D. E. et al.; WO9706799), ammonium acetate (3.0 g, 39 mmol) and NaCNBH3 (491 mg, 7.8 mmol) in 25 mL of dry methanol was stirred for 2 days at RT. The solvent was removed and the residue was acidified to pH 2 to destroy the excess NaCNBH3. After basification with aq Na2CO3 to pH 10, the product was extracted into ether. The ether layer was dried (K2CO3) and the solvent was evaporated to provide 330 mg of the racemic 4-amino-2-methyltetrahydroisoquinoline. 1H NMR (CDCl3): δ 2.20 (bs, 2H, NH2), δ 2.60 (s, 3H, NCH3), δ 2.90 (d, 2H, CHCH2N), δ 3.55 (d, 1H, ArCH2N), δ 3.90 (d, 1H, ArCH2N), δ 4.15 (t, 1H, ArCHN), δ 7.20-7.60 (m, 4H, ArH).

Workup

  1. customThe solvent was removed
  2. customto destroy the excess NaCNBH3
  3. extractionAfter basification with aq Na2CO3 to pH 10, the product was extracted into ether
  4. dry with materialThe ether layer was dried (K2CO3)
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-78ee34147ec944c987b6ce1b77ff1ec3
Source dataset
uspto-grants-2005_07
Patent number
US06919347B2

Reaction notes

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