Aniline → HCID 178486196, compound

HRID 1490283Notes

Reaction equation

HRID 1490283 reaction equation
[F:1][C:2]1[CH:18]=[CH:17][C:16]2[N:15]([CH3:19])[C:14]3[C:6]([N:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)=[C:5]([Cl:20])[C:4]=2[CH:3]=1.[NH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>C(OCCO)C.C(OCC)C>[ClH:20].[F:1][C:2]1[CH:18]=[CH:17][C:16]2[NH+:15]([CH3:19])[C:14]3[C:6]([N:7]=[C:8]4[C:13]=3[CH:12]=[CH:11][CH:10]=[CH:9]4)=[C:5]([NH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 6115AnilineHCID 67598476HCID 67598476, compound

Product 1

HCID 178486196HCID 178486196, compoundYield 81.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 2-fluoro-5-methyl-11-chloroquindoline from Example 24 (530 mg, 1.79 mmol) and aniline (0.75 g, 8.06 mmol) in EtOCH2CH2OH (50 mL) was heated at 120° C. for 10 min. During this time the color of the reaction mixture changed from purple to yellow, and a yellow precipitate formed. After cooling, the reaction mixture was diluted with diethyl ether (100 mL) and the precipitate was collected, washed thoroughly with diethyl ether and dried, providing 555 mg (79.4%) of the title compound, mp 280° C. (sublimed); 1H NMR (DMSO-d6) δ 11.26 (s, NH), 10.62 (s, NH), 8.64 (d, J=8.0, 2H), 8.46 (d, J=9.2, 1H), 8.04 (t, J=8.0, 1H), 7.77-7.68 (m, 2H), 7.47-7.39 (m, 3H), 7.29-7.22 (m, 3H), 4.81 (s, 3H); 13C NMR (acetone-d6) δ 152.50 (d, J=259.5), 136.01, 132.03 (d, J=2.96), 130.95, 130.52, 127.76, 125.68, 123.12, 119.52, 117.72, 115.57, 115.32, 115.08, 113.86 (d, J=9.6), 113.37, 112.07 (d, J=9.7), 107.81, 106.57, 101.60 (d, J=26.2), 32.13; MS (EI, m/z) 340 (M+).

Workup

  1. customformed
  2. temperatureAfter cooling
  3. customthe precipitate was collected
  4. washwashed thoroughly with diethyl ether
  5. customdried

Sources & evidence

ORD record
ord-383e27d9c0c942a58042f4998613a904
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

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