Ammonium Hydroxide → HCID 54549569, compound

HRID 1504950Notes

Reaction equation

HRID 1504950 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([O:13]C)=O)=[CH:4][CH:3]=1.[NH4+:15].[OH-]>CO>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][CH2:10][C:11]([NH2:15])=[O:13])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 88628Methyl 4-aminobenzenebutanoate

Product 1

HCID 54549569HCID 54549569, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of compound 27 (300 mg, 1.55 mmol) in CH3OH (5 mL) was added NH4OH (32) at room temperature with stirring. The reaction mixture was stirred at room temperature for 6 h and concentrated in vacuo. The residue was diluted with water and extracted with DCM/CH3OH (10:1). The combined organic layers were dried over Na2SO4 and concentrated to dryness to give compound 33 (194 mg, 70%) as a white solid. The crude product was used directly for the next step without purification.

Workup

  1. stirringThe reaction mixture was stirred at room temperature for 6 h
  2. concentrationconcentrated in vacuo
  3. additionThe residue was diluted with water
  4. extractionextracted with DCM/CH3OH (10:1)
  5. dry with materialThe combined organic layers were dried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-dfc911b0f96a4bae878ba53802b70ee4
Source dataset
uspto-grants-2015_12
Patent number
US09216957B2

Reaction notes

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