Potassium Carbonate → HCID 86638178, compound

HRID 1514978Notes

Reaction equation

HRID 1514978 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([CH3:10])[C:5]([CH:6]=[O:7])=[C:4]([CH3:11])[CH:3]=1.[CH3:12][O:13][C:14](=[O:17])[CH2:15]Br.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:12][O:13][C:14](=[O:17])[CH2:15][NH:1][C:2]1[CH:3]=[C:4]([CH3:11])[C:5]([CH:6]=[O:7])=[C:8]([CH3:10])[CH:9]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 60984Methyl bromoacetate2×HCID 123812354-Amino-2,6-dimethylbenzaldehyde

Product 1

HCID 86638178HCID 86638178, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 4-amino-2,6-dimethylbenzaldehyde (600 mg) and bromoacetic acid methyl ester (0.4 mL) in DMF (20 mL) was added K2CO3 (1.4 g) and the suspension was heated at 80° C. After 1 h, additional bromoacetic acid methyl ester (0.4 mL) was added and this process was continued until the starting material was consumed (check by LC/MS). The reaction mixture was partioned between water and EtOAc. The aqueous layer was extracted with EtOAc. The combined organic layers were dried, filtered and concentrated and the residue was purified by flash chromatography using hexanes/ethyl acetate (2:1) to give (4-formyl-3,5-dimethylphenylamino)-acetic acid methyl ester as a yellow solid. MS (ESI)m/z 222 (M+H).

Workup

  1. customwas consumed (check by LC/MS)
  2. extractionThe aqueous layer was extracted with EtOAc
  3. customThe combined organic layers were dried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customthe residue was purified by flash chromatography

Sources & evidence

ORD record
ord-68c242285682498d80dcebc693837bf1
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

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