Methyl 4-(2-cyanophenyl)benzoate → 4-(2'-Aminomethylphenyl)hydroxymethylbenzene

HRID 1422351Notes

Reaction equation

HRID 1422351 reaction equation
C[O:2][C:3](=O)[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]#[N:17])=[CH:6][CH:5]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[NH2:17][CH2:16][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[C:7]1[CH:6]=[CH:5][C:4]([CH2:3][OH:2])=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 1393412Methyl 4-(2-cyanophenyl)benzoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 108999664-(2'-Aminomethylphenyl)hydroxymethylbenzene

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 4-(2'-cyanophenyl)benzoic acid methyl ester (0.428 g, 1.804 mmol) in tetrahydrofuran (14.3 mL) at 0° C. was added 1.0 M lithium aluminum hydride in tetrahydrofuran (3.61 mL, 3.61 mmol) over 10 minutes. The reaction was allowed to stir at ambient temperature for 3 hours, then warmed to 45° C. for 3 hours, cooled and quenched by dropwise addition of saturated Na2SO4 (0.46 mL). The reaction was diluted with diethylether, Na2SO4 was added, the mixture filtered through a pad of Celite and the filtrate evaporated in vacuo to afford the title compound.

Workup

  1. temperaturewarmed to 45° C. for 3 hours
  2. temperaturecooled
  3. customquenched by dropwise addition of saturated Na2SO4 (0.46 mL)
  4. additionThe reaction was diluted with diethylether, Na2SO4
  5. additionwas added
  6. filtrationthe mixture filtered through a pad of Celite
  7. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-b3a2f61e576840cb84c614cb212bdb91
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

Loading…