Aluminium lithium hydride → 3-(Isobutylamino)-4-nitrobenzaldehyde

HRID 250733Notes

Reaction equation

HRID 250733 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].CN(OC)[C:9](=[O:24])[C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[C:12]([NH:19][CH2:20][CH:21]([CH3:23])[CH3:22])[CH:11]=1>O1CCCC1>[CH2:20]([NH:19][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[N+:16]([O-:18])=[O:17])[CH:9]=[O:24])[CH:21]([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 86067101HCID 86067101, compound

Product 1

HCID 860671033-(Isobutylamino)-4-nitrobenzaldehydeYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

Add lithium aluminum hydride (4.4 mL, 1 M in tetrahydrofuran) dropwise to a solution of N-[methyl]-N-[methoxy]-3-(isobutylamino)-4-nitrobenzamide (1.18 g, 4.2 mmol) in 20 mL of dry tetrahydrofuran at −78° C. Warm the mixture to −30° C. over 2 hours, and then to 0° C. over 30 minutes. Cool to −70° C. and carefully quench with 30 mL 5% aqueous potassium hydrogensulfate, warm to 0° C., and dilute with ethyl acetate. Separate the phases, dry the organic phase over magnesium sulfate and concentrate under reduced pressure to provide the desired benzaldehyde (70%).

Workup

  1. temperatureCool to −70° C.
  2. customcarefully quench with 30 mL 5% aqueous potassium hydrogensulfate
  3. temperaturewarm to 0° C.
  4. additiondilute with ethyl acetate
  5. customSeparate the phases
  6. dry with materialdry the organic phase over magnesium sulfate
  7. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-6d849626c78340039761c890be9593e6
Source dataset
uspto-grants-2011_01
Patent number
US07863310B2

Reaction notes

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