Methyl acetoacetate → HCID 10060315, compound

HRID 266695Notes

Reaction equation

HRID 266695 reaction equation
[OH-:1].[K+].C(OC)(=O)[CH2:4][C:5]([CH3:7])=O.[NH2:11][C:12]1[CH:18]=[C:17]([Cl:19])[C:16]([Cl:20])=[CH:15][C:13]=1[NH2:14].O.[CH3:22]O>C1(C)C(C)=CC=CC=1>[C:5]([N:14]1[C:13]2[CH:15]=[C:16]([Cl:20])[C:17]([Cl:19])=[CH:18][C:12]=2[NH:11][C:22]1=[O:1])([CH3:7])=[CH2:4]

Participants

6

Reactant 4

HCID 7757Methyl acetoacetateHCID 14797Potassium HydroxideHCID 792974,5-Dichloro-1,2-phenylenediamineHCID 22242641Methanol--water (1/1)

Product 1

HCID 10060315HCID 10060315, compound

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Conditions

Temperature
120 °C

Procedure

0.3 ml of 47% potassium hydroxide and 160 mmol of methyl acetoacetate in 20 ml of xylene are successively added to 150 mmol of 2-amino-4,5-dichloroaniline in 50 ml of xylene, stirred at 120° C. The whole mixture is brought to reflux for 4 hours, the water/methanol mixture formed being removed by means of a Dean and Stark apparatus. After addition of 26 ml of 47% potassium hydroxide and 17 ml of water, the aqueous phase is washed with xylene and then neutralized with acetic acid. The expected product crystallizes and is filtered off, washed and dried.

Workup

  1. temperatureto reflux for 4 hours
  2. custombeing removed by means of a Dean and Stark apparatus
  3. additionAfter addition of 26 ml of 47% potassium hydroxide and 17 ml of water
  4. washthe aqueous phase is washed with xylene
  5. customThe expected product crystallizes
  6. filtrationis filtered off
  7. washwashed
  8. customdried

Sources & evidence

ORD record
ord-e817da409b744271b301b62c275577a2
Source dataset
uspto-grants-1997_07
Patent number
US05652246

Reaction notes

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