2-tert-Butylaniline → HCID 67208015, compound

HRID 1042984Notes

Reaction equation

HRID 1042984 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[C:13]([CH3:18])=[N:14][O:15][C:16]=3[CH3:17])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20].[C:22]([C:26]1[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=1[NH2:28])([CH3:25])([CH3:24])[CH3:23]>CC#N>[C:22]([C:26]1[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=1[NH:28][C:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]3[C:13]([CH3:18])=[N:14][O:15][C:16]=3[CH3:17])=[CH:9][CH:10]=2)[N:5]=[CH:4][C:3]=1[N+:19]([O-:21])=[O:20])([CH3:25])([CH3:23])[CH3:24]

Participants

4

Reactant 2

HCID 805742-tert-ButylanilineHCID 57465578HCID 57465578, compound2×

Product 1

HCID 67208015HCID 67208015, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 4-chloro-7-(3,5-dimethyl-4-isoxazolyl)-3-nitroquinoline (for a preparation see Intermediate 16) (2.2 g, 7.2 mmol) and 2-tert-butylaniline (1.2 g, 8 mmol) in CH3CN (20 ml) was refluxed for 1 h. The solvent was evaporated in vacuo and the residue treated with an aqueous solution of sodium hydroxide N, extracted with DCM, washed with water and dried over Na2SO4. The residue was purified by chromatography on silica gel eluting with DCM/MeOH (99:1) to give the title compound as a yellow solid (2.4 g, 80%). [APCI-MS] m/z: 417 MH+, Rt 3.73 min. NMR (300 MHz, DMSO-d6, ppm) δ: 9.87 (brs, 1H), 8.92 (s, 1H), 8.34 (d, J=8.7 Hz, 1H), 7.82 (s, 1H), 7.50 (d, J=8.9 Hz, 1H), 7.25-6.91 (m, 4H), 2.32 (s, 3H), 2.15 (s, 3H).

Workup

  1. temperaturewas refluxed for 1 h
  2. customThe solvent was evaporated in vacuo
  3. additionthe residue treated with an aqueous solution of sodium hydroxide N
  4. extractionextracted with DCM
  5. washwashed with water
  6. dry with materialdried over Na2SO4
  7. customThe residue was purified by chromatography on silica gel eluting with DCM/MeOH (99:1)

Sources & evidence

ORD record
ord-10e6e130609c48f492ff3869c2079111
Source dataset
uspto-grants-2013_10
Patent number
US08557984B2

Reaction notes

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