Ammonium Acetate → Sodium Hydroxide

HRID 1729338Notes

Reaction equation

HRID 1729338 reaction equation
[CH2:1]([C:5]1[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]#[N:25])=[CH:14][CH:13]=2)[C:9](=[O:26])[C:8]([CH:27]=O)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].C([O-])(=[O:31])C.[NH4+].[BH3-]C#[N:36].[Na+:37]>C(O)(C)C>[NH2:36][CH2:27][C:8]1[C:9](=[O:26])[N:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[C:24]#[N:25])=[CH:14][CH:13]=2)[C:5]([CH2:1][CH2:2][CH2:3][CH3:4])=[CH:6][CH:7]=1.[OH-:31].[Na+:37]

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 5003444Sodium cyanoborohydrideHCID 19012335HCID 19012335, compound

Product 2

HCID 14798Sodium HydroxideHCID 11824845HCID 11824845, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A suspension of 370 mg of 6-butyl-1-(2'-cyanobiphenyl-4-ylmethyl)-3-formyl-1,2-dihydro-2-oxopyridine, 770 mg of ammonium acetate, 61 mg of NaBH3CN and 400 mg of a powdered 3 Å molecular sieve in 10 ml of isopropanol is stirred under argon for 3 days at 20°. It is filtered, the material on the filter is washed with methanol and the filtrate is evaporated. 3-Aminomethyl-6-butyl-1-(2'-cyanobiphenyl-4-ylmethyl)-1,2-dihydro-2-oxopyridine is obtained after conventional working-up (sodium hydroxide solution/methylene chloride), m.p. 118°.

Workup

  1. filtrationIt is filtered
  2. washthe material on the filter is washed with methanol
  3. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-2a998198e6544db0add701c5c690b928
Source dataset
uspto-grants-1994_07
Patent number
US05332750

Reaction notes

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