Hydrochloric Acid → HCID 178516753, compound

HRID 2060250Notes

Reaction equation

HRID 2060250 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=O)[CH:9]=O)=[CH:4][CH:3]=1.[NH2:12][CH2:13][C:14]([NH2:16])=[O:15].[OH-].[Na+].Cl.C(=O)(O)[O-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:12]=[CH:13][C:14]([OH:15])=[N:16][CH:9]=2)=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 69020GlycinamideHCID 269588(4-Chlorophenyl)(oxo)acetaldehydeHCID 516892Sodium Bicarbonate

Product 1

HCID 178516753HCID 178516753, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
-30 °C

Procedure

To a stirred solution of (4-chloro-phenyl)-oxo-acetaldehyde (300 mg, 1.69 mmol) in methanol (15 mL) was added 2-amino-acetamide (187 mg, 1.69 mmol). The resulting mixture was cooled to −30° C. and 12.5M aqueous sodium hydroxide solution (0.3 mL) added. The resulting mixture was allowed to warm to −5° C. and was stirred at this temperature for 2 hours, followed by stirring at room temperature for 2 hours. Concentrated aqueous hydrogen chloride (0.3 mL) was added, followed by saturated sodium bicarbonate solution (1.0 mL). The reaction mixture was filtered and the resulting solid was washed with water (10 mL) and dried in a vacuum oven to afford the title compound as a brown solid (130 mg, 37%)

Workup

  1. temperatureto warm to −5° C.
  2. stirringby stirring at room temperature for 2 hours
  3. filtrationThe reaction mixture was filtered
  4. washthe resulting solid was washed with water (10 mL)
  5. customdried in a vacuum oven

Sources & evidence

ORD record
ord-bacc7dfb8db14fada60bd2545ce4e55c
Source dataset
uspto-grants-2012_10
Patent number
US08278343B2

Reaction notes

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