Ethanol → HCID 15053099, compound

HRID 1087051Notes

Reaction equation

HRID 1087051 reaction equation
C(O)C.[NH:4]1[C:12]2[C:7](=[CH:8][C:9]([NH2:13])=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.Cl[C:15]1[CH:20]=[CH:19][N:18]=[CH:17][C:16]=1[N+:21]([O-:23])=[O:22]>C(N(CC)CC)C>[N+:21]([C:16]1[CH:17]=[N:18][CH:19]=[CH:20][C:15]=1[NH:13][C:9]1[CH:8]=[C:7]2[C:12](=[CH:11][CH:10]=1)[NH:4][CH:5]=[CH:6]2)([O-:23])=[O:22]

Participants

5

Reactant 3

HCID 702EthanolHCID 788675-AminoindoleHCID 27357814-Chloro-3-nitropyridine

Product 1

HCID 15053099HCID 15053099, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
60 °C

Procedure

To 150 ml of absolute ethanol were added 1H-indol-5-amine (8.06 g), 4-chloro-3-nitropyridine (10.0 g) and triethylamine (8.5 ml), and this mixture was heated to 60° C. and stirred for 2 hours. The mixture was cooled, the ethanol evaporated, and the residue taken up in a water/ethyl acetate mixture. This was treated with Na2CO3 (aq) to adjust the pH to 10. The organic layer was collected, the aqueous layer extracted again with ethyl acetate, and the organics were combined, washed with water and dried (sat. NaCl, anh. MgSO4).

Workup

  1. temperatureThe mixture was cooled
  2. customthe ethanol evaporated
  3. additionThis was treated with Na2CO3 (aq)
  4. customThe organic layer was collected
  5. extractionthe aqueous layer extracted again with ethyl acetate
  6. washwashed with water
  7. dry with materialdried (sat. NaCl, anh. MgSO4)

Sources & evidence

ORD record
ord-bea27084743446739ee96bef9ad51e33
Source dataset
uspto-grants-1991_07
Patent number
US05034403

Reaction notes

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