dimethyl 2-aminoisophthalate → HCID 70433476, compound

HRID 986247Notes

Reaction equation

HRID 986247 reaction equation
[NH2:1][C:2]1[C:11]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6]C)=O.C(O[C:19](OCC)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[Cl:27])[CH3:20])C>>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[C:19]1[CH2:20][C:4](=[O:6])[C:3]2[C:2](=[C:11]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=[CH:9][CH:8]=2)[N:1]=1

Participants

3

Reactant 2

HCID 12217545dimethyl 2-aminoisophthalateHCID 20158450HCID 20158450, compound

Product 1

HCID 70433476HCID 70433476, compoundYield 23.3%

Conditions

Temperature
140 °C

Procedure

Alternatively, to 8 grams of dimethyl 2-aminoisophthalate was added 9.2 grams of o-chloroacetophenone diethylacetal, the mixture was heated at 140° C. for 30 minutes, then at 200° C. for additional 20 minutes, and finally heated to reflux for 18 hours. The reaction mixture was cooled, crystals separated out were collected by filtration, and recrystallized from acetone to give 2.8 grams of the title product, melting point 166°-168° C.

Workup

  1. temperaturefinally heated
  2. temperatureto reflux for 18 hours
  3. temperatureThe reaction mixture was cooled
  4. customcrystals separated out
  5. filtrationwere collected by filtration
  6. customrecrystallized from acetone

Sources & evidence

ORD record
ord-6a38e70734844918a7c64ca4d43f74ae
Source dataset
uspto-grants-1987_12
Patent number
US04711898

Reaction notes

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