Water → HCID 66880495, compound

HRID 476154Notes

Reaction equation

HRID 476154 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([Cl:12])[CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:13]([O-:15])=[O:14].[NH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([CH3:27])([CH3:26])[C:24]#[N:25])=[CH:19][CH:18]=1.O>C(O)(=O)C>[Cl:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][CH:8]=1)[N:5]=[CH:4][C:3]([N+:13]([O-:15])=[O:14])=[C:2]2[NH:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]([CH3:27])([CH3:26])[C:24]#[N:25])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 100578012-(4-Aminophenyl)-2-methylpropanenitrileHCID 10681670Quinoline, 4,6-dichloro-3-nitro-

Product 1

HCID 66880495HCID 66880495, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 4,6-dichloro-3-nitroquinoline (Compound of Preparation E, 4.0 g, 16.46 mmol) and 2-(4-aminophenyl)-2-methylpropanenitrile (2.63 g, 16.46 mmol) in acetic acid (350 ml) was stirred for 2 hours. Water was added and the yellow precipitate was filtered off, washed with water and saturated aqueous NaHCO3. The yellow solid was dried to obtain the title compound. Yield: 5 g (83%); 1H NMR (DMSO-d6, 300 MHz): δ 10.074 (s, 1H), 9.062 (s, 1H,), 8.552-8.558 (d, 1H, J=1.8 Hz), 7.995-8.025 (d, 1H, J=9 Hz), 7.875-7.912 (t, 1H), 7.437-7.466 (d, 2H, J=8.4 Hz), 7.100-7.128 (d, 2H, J=8.4 Hz), 1.664 (s, 6H).

Workup

  1. filtrationthe yellow precipitate was filtered off
  2. washwashed with water and saturated aqueous NaHCO3
  3. customThe yellow solid was dried

Sources & evidence

ORD record
ord-bc56c849829c446ea468e4d262fb47fd
Source dataset
uspto-grants-2014_01
Patent number
US08637670B2

Reaction notes

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