Ammonium Acetate → HCID 86686027, compound

HRID 2277731Notes

Reaction equation

HRID 2277731 reaction equation
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6](=[O:24])[N:7]([C:13]3[C:22]4[CH2:21][CH2:20][CH2:19][C:18](=O)[C:17]=4[CH:16]=[N:15][CH:14]=3)[C:8]2([CH3:12])[CH3:11])=[CH:4][CH:3]=1.[BH3-]C#[N:27].[Na+].CC([O-])=O.[NH4+]>C(O)(C)C>[NH2:27][CH:18]1[C:17]2[CH:16]=[N:15][CH:14]=[C:13]([N:7]3[C:8]([CH3:12])([CH3:11])[C:9]4[C:5](=[CH:4][CH:3]=[C:2]([Cl:1])[CH:10]=4)[C:6]3=[O:24])[C:22]=2[CH2:21][CH2:20][CH2:19]1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 86686025HCID 86686025, compound

Product 1

HCID 86686027HCID 86686027, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-(6-chloro-1,1-dimethyl-3-oxo-1,3-dihydro-isoindol-2-yl)-6,7-dihydro-5H-isoquinolin-8-one (408 mg, 1.2 mmol), NaBH3CN (75 mg, 1.2 mmol) and CH3COONH4 (1.0 g, 12 mmol) in isopropanol (10 mL) was heated to reflux for 3 hours. After cooling to room temperature, it was concentrated to afford a yellowish oil which was extracted between water with EtOAc (2×100 mL). The combined organic layers were washed with brine, dried over anhy. Na2SO4, filtered and concentrated in vacuo to afford the crude title compound (327 mg, 80%) as a brown solid. MS: 342.1 & 325.1 (M+H+).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 hours
  3. concentrationit was concentrated
  4. customto afford a yellowish oil which
  5. extractionwas extracted between water with EtOAc (2×100 mL)
  6. washThe combined organic layers were washed with brine
  7. customdried over anhy
  8. filtrationNa2SO4, filtered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f2e00e4e63624e38a542792e22408803
Source dataset
uspto-grants-2015_09
Patent number
US09133158B2

Reaction notes

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