Acetic Acid → HCID 59558570, compound

HRID 1959295Notes

Reaction equation

HRID 1959295 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:10]=O)=[C:6]([CH:9]=1)[C:7]#[N:8].[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClC(Cl)C.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:10][N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5049666Sodium triacetoxyborohydrideHCID 534050365-Bromo-2-formylbenzonitrile

Product 1

HCID 59558570HCID 59558570, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of 5-bromo-2-formylbenzonitrile (200 mg, 0.95 mmol) and morpholine (248 mg, 2.85 mmol) in dichloroethane (10 mL), acetic acid (342 mg, 5.7 mmol) was added and reaction stirred at room temperature for 30 minutes. Then sodium triacetoxyborohydride (604 mg, 2.85 mmol) was added to the reaction mixture at 0° C., allowed to attain room temperature and stirring continued for overnight. On completion, reaction mixture was diluted with dichloromethane, washed with water, saturated aqueous sodium bicarbonate solution and dried over sodium sulphate. Removal of the solvent under reduced pressure followed by column chromatographic purification afforded the desired compound (150 mg, 56%).

Workup

  1. customreaction
  2. customto attain room temperature
  3. stirringstirring
  4. waitcontinued for overnight
  5. customOn completion, reaction mixture
  6. washwashed with water, saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over sodium sulphate
  8. customRemoval of the solvent under reduced pressure
  9. customfollowed by column chromatographic purification

Sources & evidence

ORD record
ord-800ba6c566f642189361cf40ee16c013
Source dataset
uspto-grants-2013_04
Patent number
US08410088B2

Reaction notes

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