2-Aminoterephthalic acid → HCID 57516453, compound

HRID 520819Notes

Reaction equation

HRID 520819 reaction equation
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([OH:13])=[O:12])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O>C1(OC2C=CC=CC=2)C=CC=CC=1.C1(=O)CCCCC1>[O:6]=[C:4]1[C:3]2[CH:7]=[CH:8][C:9]([C:11]([OH:13])=[O:12])=[CH:10][C:2]=2[NH:1][C:3]2[CH2:7][CH2:8][CH2:9][CH2:10][C:2]1=2

Participants

4

Reactant 1

HCID 27248222-Aminoterephthalic acid

Product 1

HCID 57516453HCID 57516453, compound

Reagents, catalysts & solvents 2

HCID 7583Diphenyl EtherSolventHCID 7967CyclohexanoneSolvent2×

Conditions

Temperature
250 °C

Procedure

To a suspension of 2-amino terephthalic acid (12 g, 6.6 mmols) in diphenyl ether (120 mL), cyclohexanone (25 mL) was added and the reaction mixture was heated to 250° C. for 10 min. Reaction completion was monitored by LC/MS (75% starting material and 25% Product formation was observed). Cyclohexanone (25 mL) was added and the reaction mixture was heated to 250° C. for another 10 min. (LC/MS showed 50% product formation). The above process was repeated till LC/MS showed complete product formation (Starting material <2%). The reaction mixture was cooled to 25° C., product was filtered, washed with hexane (100 mL) and dried under vacuum to get 15.8 g of (Via) (98%) as a yellow solid.

Workup

  1. additionwas added
  2. customReaction completion
  3. temperatureThe reaction mixture was cooled to 25° C.
  4. filtrationproduct was filtered
  5. washwashed with hexane (100 mL)
  6. customdried under vacuum
  7. customto get 15.8 g of (Via) (98%) as a yellow solid

Sources & evidence

ORD record
ord-180e7a29ffa640f6a54e1a4090cba6a0
Source dataset
uspto-grants-2016_05
Patent number
US09328093B2

Reaction notes

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