Aluminium lithium hydride → 3,6-dimethyl-4-N-(pentan-3-yl)-2-N-(2,4,6-trimethylphenyl)pyridine-2,4-diamine

HRID 968014Notes

Reaction equation

HRID 968014 reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[C:12]([C:13](O)=O)=[C:11]([NH:16][C:17]2[C:22]([CH3:23])=[CH:21][C:20]([CH3:24])=[CH:19][C:18]=2[CH3:25])[N:10]=[C:9]([CH3:26])[CH:8]=1)[CH2:4][CH3:5])[CH3:2].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C(OCC)C.[Cl-].[Cl-].[Cl-].[Al+3]>[CH2:1]([CH:3]([NH:6][C:7]1[CH:8]=[C:9]([CH3:26])[N:10]=[C:11]([NH:16][C:17]2[C:18]([CH3:25])=[CH:19][C:20]([CH3:24])=[CH:21][C:22]=2[CH3:23])[C:12]=1[CH3:13])[CH2:4][CH3:5])[CH3:2]

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 248062594-(1-Ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-nicotinic acid

Product 1

HCID 219122043,6-dimethyl-4-N-(pentan-3-yl)-2-N-(2,4,6-trimethylphenyl)pyridine-2,4-diamine

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6451240Aluminum(III) ChlorideSolvent

Procedure

The title compound was prepared by reduction of 4-(1-ethyl-propylamino)-6-methyl-2-(2,4,6-trimethyl-phenylamino)-nicotinic acid with 1M of lithium aluminum hydride in diethyl ether and aluminum trichloride at reflux. 1H NMR(CDCl3)6.9(s,2H), 6.0(s,1H), 5.4(brs,1H), 3.6(d,1H), 3.3(m,1H), 2.32(s,3H), 2.2(s,3H), 2.15(s,6H), 1.4-1.7(m,4H), 1.0(t,6H) ppm.

Workup

  1. temperatureat reflux

Sources & evidence

ORD record
ord-df5bc725889b4b709405fc701256820e
Source dataset
uspto-grants-2005_10
Patent number
US06956047B1

Reaction notes

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