Water → HCID 22170232, compound

HRID 1822872Notes

Reaction equation

HRID 1822872 reaction equation
[NH2:1][C:2]1[C:3]([CH2:12][CH3:13])=[C:4]([CH:9]=[CH:10][CH:11]=1)[C:5](OC)=[O:6].[H-].[Al+3].[Li+].[H-].[H-].[H-].O>C1COCC1>[NH2:1][C:2]1[C:3]([CH2:12][CH3:13])=[C:4]([CH2:5][OH:6])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 962WaterHCID 21226445Aluminium lithium hydrideHCID 22170201HCID 22170201, compound

Product 1

HCID 22170232HCID 22170232, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-amino-2-ethylbenzoate (0.83 g, 4.63 mmol), in THF (40 ml) was added Lithium aluminium hydride (0.9 g, 23.7 mmol). The mixture was heated at 50 C. for 5 h, cooled to 0 C. and hydrolysed cautiously with water. The slurry was extracted with EtOAc (×5). The extracts were washed with brine, dried Na2SO4, and evaporated. The residue was purified by chromatography (CH2Cl2/MeOH) to give the title compound 0.63 g (89%) as a white powder.

Workup

  1. temperatureThe mixture was heated at 50 C
  2. temperaturecooled to 0 C
  3. extractionThe slurry was extracted with EtOAc (×5)
  4. washThe extracts were washed with brine, dried Na2SO4
  5. customevaporated
  6. customThe residue was purified by chromatography (CH2Cl2/MeOH)

Sources & evidence

ORD record
ord-a9d2c71466414e4ea5eb150388f3719c
Source dataset
uspto-grants-2006_05
Patent number
US07037925B2

Reaction notes

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