2-Nitropropane → HCID 54195305, compound

HRID 396358Notes

Reaction equation

HRID 396358 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:12]=[C:11]([CH:13]=[O:14])[C:10]2[C:5](=[C:6]([C:15]([F:18])([F:17])[F:16])[CH:7]=[CH:8][CH:9]=2)[N:4]=1.[N+:21]([CH:24]([CH3:26])[CH3:25])([O-:23])=[O:22]>C(Cl)Cl>[N+:21]([C:24]([CH:13]([C:11]1[C:10]2[C:5](=[C:6]([C:15]([F:18])([F:16])[F:17])[CH:7]=[CH:8][CH:9]=2)[N:4]=[C:3]([C:2]([F:19])([F:1])[F:20])[CH:12]=1)[OH:14])([CH3:26])[CH3:25])([O-:23])=[O:22]

Participants

4

Reactant 2

HCID 3982-NitropropaneHCID 122545692,8-Bis(trifluoromethyl)-4-quinolinecarboxaldehyde

Product 1

HCID 54195305HCID 54195305, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 2,8-bis(trifluoromethyl)-4-quinolinecarboxaldehyde (200 mg, 0.85 mmol), 2-nitropropane (0.1 mL, 1.1 mmol) and Amberlyst 21 resin (200 mg) was stirred at room temperature for 17 h, treated with CH2Cl2 (3 mL), filtered to remove the resin, the filtrate concentrated in vacuo to give a viscous oil which was crystallised from heptane to give a white solid which was recrystallised (ether/heptane) to give the product (140 mg, 51%) as a white crystalline solid: IR νmax (Nujol)/cm−1 3484, 2923, 1544, 1311, 1134 and 780; NMR δH (400 MHz, CDCl3) 1.37 (3H, s), 1.54 (3H, s), 3.03 (1H, d, J 4.5 Hz),6.36 (1H, d, J 4.4 Hz), 7.80 (1H, t, J 8.1 Hz), 8.07 (1H, s), 8.21 (1H, d, J 7.1 Hz) and 8.44 (1H, d, J 8.5 Hz).

Workup

  1. filtrationfiltered
  2. customto remove the resin
  3. concentrationthe filtrate concentrated in vacuo
  4. customto give a viscous oil which
  5. customwas crystallised from heptane
  6. customto give a white solid which
  7. customwas recrystallised (ether/heptane)

Sources & evidence

ORD record
ord-888e26de11314ac7a286a949bac880fe
Source dataset
uspto-grants-2003_08
Patent number
US06608085B1

Reaction notes

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