Aluminium lithium hydride → HCID 18467691, compound

HRID 2229426Notes

Reaction equation

HRID 2229426 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N-:8][CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=2)=[C:4]([N+:22]([O-])=O)[CH:3]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>CCOCC>[NH2:22][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[NH:8][CH2:9][C:10]1[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([O:20][CH3:21])[CH:11]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86758355HCID 86758355, compound

Product 1

HCID 18467691HCID 18467691, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

N-(4-Fluoro-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 16 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. Flash-chromatography (hexane:ethylacetate 1:1) and subsequent recrystallisation from ethanol yield the title product.

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. customFlash-chromatography (hexane:ethylacetate 1:1) and subsequent recrystallisation from ethanol

Sources & evidence

ORD record
ord-ceb6206928db497eb9ae47a845eac303
Source dataset
uspto-grants-2002_07
Patent number
US06420410B1

Reaction notes

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