Formic Acid → HCID 14989625, compound

HRID 727768Notes

Reaction equation

HRID 727768 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2.[CH:17](O)=[O:18].C1(N=C=NC2CCCCC2)CCCCC1>C1COCC1>[NH:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:16]=[C:8]1[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][CH:17]=[O:18]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 10868DicyclohexylcarbodiimideHCID 7359662-(2-Aminophenyl)indole

Product 1

HCID 14989625HCID 14989625, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution prepared from 20 g of 2-(2-aminophenyl)indole, 12.7 ml of formic acid and 500 ml of THF was added 26 g of dicyclohexyl carbodiimide at room temperature under N2. The resultant solution was stirred overnight at room temperature. The mixture was then filtered and the filtrate washed with aqueous NaHCO3 (2x), H2O and saturated NaCl solution and dried (MgSO4). Concentration gave a red oil which was purified by HPLC, using 1% EtOAc/CH2Cl2 as an eluent, to afford 11.45 g of solid, m.p. 147°-149° C.

Workup

  1. filtrationThe mixture was then filtered
  2. washthe filtrate washed with aqueous NaHCO3 (2x), H2O and saturated NaCl solution
  3. dry with materialdried (MgSO4)
  4. concentrationConcentration
  5. customgave a red oil which
  6. customwas purified by HPLC

Sources & evidence

ORD record
ord-80fc1e47fe66443ab185752fe8af2ce8
Source dataset
uspto-grants-1991_09
Patent number
US05045539

Reaction notes

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