Aluminium lithium hydride → HCID 18467687, compound

HRID 2229427Notes

Reaction equation

HRID 2229427 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N-:9][CH2:10][C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)=[C:5]([N+:23]([O-])=O)[CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[NH2:23][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[CH:8]=[CH:7][C:6]=1[NH:9][CH2:10][C:11]1[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86758356HCID 86758356, compound

Product 1

HCID 18467687HCID 18467687, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

[N-(4-methoxy-2-nitrophenyl)]3,4,5-trimethoxybenzylamide (17.1 mmol, 6.0 g) in absolute ether (100 ml) is added to LiAlH4 (63.4 mmol, 2.4 g) in absolute ether (40 ml), and the mixture is stirred at room temperature for 8-9 hours. While cooling with an ice bath, the suspension is quenched with water (40 ml) and is extracted with ether (3×100 ml). The combined organic layers are dried with MgSO4, filtered and evaporated. Recrystallisation from ethanol yields the title product as a red solid (23%).

Workup

  1. temperatureWhile cooling with an ice bath
  2. customthe suspension is quenched with water (40 ml)
  3. extractionis extracted with ether (3×100 ml)
  4. dry with materialThe combined organic layers are dried with MgSO4
  5. filtrationfiltered
  6. customevaporated
  7. customRecrystallisation from ethanol

Sources & evidence

ORD record
ord-c6e47c0ae57d4e688ce9454ef16e3a84
Source dataset
uspto-grants-2002_07
Patent number
US06420410B1

Reaction notes

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