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

HRID 1831694Notes

Reaction equation

HRID 1831694 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 aluminium hydride in diethyl ether and aluminium 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-1bee32712d92448dbc0c155ea1f487bc
Source dataset
uspto-grants-2006_06
Patent number
US07067664B1

Reaction notes

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