Ammonium Hydroxide → HCID 59683367, compound

HRID 2221292Notes

Reaction equation

HRID 2221292 reaction equation
[CH3:1][N:2]([CH3:17])[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[C:15]#[N:16])[CH:6]=1)=[O:4].[NH4+].[OH-].[H][H]>[Ni].CCO>[CH3:1][N:2]([CH3:17])[C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[CH2:15][NH2:16])[CH:6]=1)=[O:4]

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 69212464HCID 69212464, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 59683367HCID 59683367, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A suspension of 5-cyano-naphthalene-2-carboxylic acid dimethylamide, 4, (18.93 g, 84.51 mmol), 28% NH4OH (24 mL) and EtOH (500 mL) is reacted with hydrogen (1 atmosphere) in the presence of Ra—Ni (8 g) catalyst for 4 days. The catalyst is removed by filtration and the filtrate is concentrated in vacuo to afford 18.66 g (97% yield) of the desired product. 1H NMR (300 MHz, CD3OD): δ 8.23 (d, J=8.7 Hz, 1H), 8.70-8.11 (m, 2H), 7.63-7.78 (m, 3H), 4.69 (s, 2H), 3.20, (s, 3H), 3.09 (s, 3H). LRMS: 228.99 (M+1), 211.96 (M+1-NH3).

Workup

  1. customThe catalyst is removed by filtration
  2. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-1160b77963b14ef3837fedebde0259db
Source dataset
uspto-grants-2008_05
Patent number
US07368462B1

Reaction notes

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