Malonic Acid → HCID 54697739, compound

HRID 897227Notes

Reaction equation

HRID 897227 reaction equation
[CH3:1][NH:2][C:3]1[CH:10]=[CH:9][C:6]([O:7][CH3:8])=[CH:5][CH:4]=1.[C:11]([OH:17])(=O)[CH2:12][C:13]([OH:15])=O.[OH-].[Na+]>>[OH:15][C:13]1[C:10]2[C:3](=[CH:4][CH:5]=[C:6]([O:7][CH3:8])[CH:9]=2)[N:2]([CH3:1])[C:11](=[O:17])[CH:12]=1

Participants

4

Reactant 3

HCID 867Malonic AcidHCID 14798Sodium HydroxideHCID 22250N-Methyl-4-anisidine

Product 1

HCID 54697739HCID 54697739, compoundYield 50%

Conditions

Temperature
90 °C

Procedure

To a mixture of N-methyl-p-anisidine (2.8 g, 20 mmol) and malonic acid (4.3 g, 40 mmol) was added POC13 (17 mL). After heating at 90° C. for 1.5 hr, the reaction mixture was poured over ice and basified with 6N NaOH to a pH of 14. The solution was then filtered and the filtrate was acidified with 6N HCl to pH 3. The precipitate was filtered and dried to afford a brown solid (1.8 g, 50%). 1H NMR (300 MHz, MeODd4) 8 3.65 (3H, s), 3.86 (3H, s), 5.97 (1H, s), 7.28 (1H, dd, J=2.8, 9.3 Hz), 7.49 (2H, d, J=9.3 Hz).

Workup

  1. filtrationThe solution was then filtered
  2. filtrationThe precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-eac06a1519b545518707d3ad5004b9c0
Source dataset
uspto-grants-2005_07
Patent number
US06921821B2

Reaction notes

Loading…