Aluminium lithium hydride → HCID 11447712, compound

HRID 1797109Notes

Reaction equation

HRID 1797109 reaction equation
C(OC(=O)[C:5]([NH:7][C:8]1[CH:13]=[CH:12][N:11]=[C:10]([C:14]2[CH2:23][CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=2)[CH:9]=1)=O)C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH:15]1[C:16]2[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:22][CH2:23][C:14]=1[C:10]1[CH:9]=[C:8]([NH:7][CH3:5])[CH:13]=[CH:12][N:11]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 69592134HCID 69592134, compound

Product 1

HCID 11447712HCID 11447712, compoundYield 42.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of N-[2-(3,4-dihydro-naphthalen-2-yl)-pyridin-4-yl]-oxalamic acid ethyl ester (0.36 g, 1.2 mmol) in THF (20 ml) was slowly added to an ice bath cooled mixture of lithium aluminum hydride (0.10 g, 2.6 mmol) in THF (20 ml). The resulting mixture was refluxed for 30 min, quenched with aqueous saturated Seignette-salt solution and extracted with AcOEt. The organic phase was dried over Na2SO4, concentrated and chromatographed (SiO2 with CH2Cl2/CH3OH/NH4OH=140/10/1) to give [2-(3,4-dihydro-naphthalen-2-yl)-pyridin-4-yl]-methyl-amine as a yellow oil (0.12 g, 42%) which was crystallized as the white fumarate salt. Mp. 106–107° C. (MeOH/Et2O), MS: m/e=236 (M+).

Workup

  1. temperaturecooled
  2. temperatureThe resulting mixture was refluxed for 30 min
  3. customquenched with aqueous saturated Seignette-salt solution
  4. extractionextracted with AcOEt
  5. dry with materialThe organic phase was dried over Na2SO4
  6. concentrationconcentrated
  7. customchromatographed (SiO2 with CH2Cl2/CH3OH/NH4OH=140/10/1)

Sources & evidence

ORD record
ord-a246aa53f3274743982f9e585640387c
Source dataset
uspto-grants-2006_04
Patent number
US07034044B2

Reaction notes

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