Water → HCID 178507424, compound

HRID 628572

Reaction equation

HRID 628572 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][C:12]([NH2:15])=[C:11]([NH2:16])[CH:10]=2)[CH:6]=[CH:5][C:4]([NH2:7])=[C:3]([NH2:8])[CH:2]=1.[NH2:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=O)=[CH:20][CH:19]=1.O>CO>[NH:15]1[C:12]2[CH:13]=[CH:14][C:9]([C:1]3[CH:6]=[CH:5][C:4]4[N:7]=[C:22]([C:21]5[CH:25]=[CH:26][C:18]([NH2:17])=[CH:19][CH:20]=5)[NH:8][C:3]=4[CH:2]=3)=[CH:10][C:11]=2[N:16]=[C:9]1[C:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 962WaterHCID 9784-Aminobenzoic AcidHCID 70713,3'-Diaminobenzidine

Product 1

HCID 178507424HCID 178507424, compoundYield 97.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
200 °C

Procedure

A homogenous mixture of biphenyl-3,3′,4,4′-tetraamine (500 mg, 2.34 mmol) and 4-aminobenzoic acid (640 mg, 4.67 mmol) was added portionwise to stirred PPA (20 mL) at 200° C. The mixture was stirred at 200° C. for 2.5 h. The mixture was cooled (to <100° C.) and poured into water. The resulting mixture was stirred until a uniform green precipitate had formed. The solid was filtered off and washed with aqueous K2CO3 and water, then dried under suction. The crude product was purified by column chromatography (99:1 EtOAc-NEt3 to 89:10:1 EtOAc-MeOH-NEt3) to afford a yellow solid. This was dissolved in MeOH and 1M HCl, and then concentrated in vacuo. The material was then ground to a fine powder and stirred in aqueous NaHCO3. The solid was filtered, washed with water and dried (vacuum oven) to give the product as a yellow solid (475 mg, 49%).

Workup

  1. additionwas added portionwise
  2. stirringThe mixture was stirred at 200° C. for 2.5 h
  3. temperatureThe mixture was cooled (to <100° C.)
  4. stirringThe resulting mixture was stirred until a uniform green precipitate
  5. customhad formed
  6. filtrationThe solid was filtered off
  7. washwashed with aqueous K2CO3 and water
  8. customdried under suction
  9. customThe crude product was purified by column chromatography (99:1 EtOAc-NEt3 to 89:10:1 EtOAc-MeOH-NEt3)
  10. customto afford a yellow solid
  11. concentration1M HCl, and then concentrated in vacuo
  12. stirringstirred in aqueous NaHCO3
  13. filtrationThe solid was filtered
  14. washwashed with water
  15. customdried (vacuum oven)

Sources & evidence

ORD record
ord-c51b80e4f4b84262a3e390909f5c44aa
Source dataset
uspto-grants-2016_04
Patent number
US09314456B2

Linked notes

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