m-Formylbenzonitrile → HCID 60917657, compound

HRID 219880Notes

Reaction equation

HRID 219880 reaction equation
[C:1]([O:5][C:6](=[O:9])[CH2:7][NH2:8])([CH3:4])([CH3:3])[CH3:2].[C:10]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH:15]=O)#[N:11].[BH4-].[Na+]>C1(C)C=CC=CC=1>[C:10]([C:12]1[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=1)[CH2:15][NH:8][CH2:7][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:9])#[N:11]

Participants

5

Reactant 3

HCID 90670m-FormylbenzonitrileHCID 151417Glycine tert-butyl esterHCID 4311764Sodium borohydride

Product 1

HCID 60917657HCID 60917657, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

To a stirred solution of glycine-ter-butyl ester (5 g, 0.038 mol) in toluene (100 mL). was added 3-cyanobenzaldehyde (5 g, 0.0381 mol) under N2 and refluxed at 140° C. for 2 h. After complete evaporation of the toluene, the reaction mass was cooled to RT and dissolved in dry methanol. Sodium borohydride (2.17 g, 0.0571 mol) was added in portions at 0° C. After 12 h, the reaction mass was evaporated under vacuum, washed with water (100 mL), extracted in DCM (100 mL), dried over sodium sulphate and concentrated under reduced pressure to afford the title compound as a yellow liquid (8.1 g, 86%). 1H NMR (DMSO-d6, 400 MHz) δ 7.71-7.72 (m, 2H), 7.63-7.65 (m, 1H), 7.53-7.55 (m, 1H), 5.40-5.41 (m, 1H), 4.53-4.54 (m, 2H), 3.17 (s, 2H), 1.39 (s, 9H).

Workup

  1. customAfter complete evaporation of the toluene
  2. temperaturethe reaction mass was cooled to RT
  3. dissolutiondissolved in dry methanol
  4. customthe reaction mass was evaporated under vacuum
  5. washwashed with water (100 mL)
  6. extractionextracted in DCM (100 mL)
  7. dry with materialdried over sodium sulphate
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-cc42d7b34395457691ce8cdd37a5cb34
Source dataset
uspto-grants-2012_06
Patent number
US08202865B2

Reaction notes

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