Phenol → HCID 86751466, compound

HRID 582648Notes

Reaction equation

HRID 582648 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.[C:21]1([OH:27])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=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]([O:27][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 996PhenolHCID 67598476HCID 67598476, compound

Product 1

HCID 86751466HCID 86751466, compoundYield 60.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8076Glycol monoethyl etherSolvent

Procedure

A solution of 2-fluoro-5-methyl-11-chloroquindoline from Example 24 (510 mg, 1.79 mmol) and phenol (1.5 g, 15.96 mmol) in EtOCH2CH2OH (50 mL) was heated at 100° 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 (150 mL) and the precipitate was collected, washed thoroughly with diethyl ether and dried, providing 410 mg (60.5%) of the title compound, mp 249.5-249.8° C.; 1H NMR (DMSO-d6) δ 12.94 (s, 1H), 8.98 (dd, J=4.4, J=10.00, 1H) 8.84 (d, J=8.4, 1H), 8.19-8.13 (m, 1H), 8.01 (dd, J=2.8, J=8.8, 1H), 7.94 (t, J=8.4, 1H), 7.77 (d, J=8.4, 1H), 7.55 (t, J=8.4, 1H), 7.44-7.40 (m, 2H), 7.22 (t, J=8.4, 1H), 7.15-7.12 (m, 2H), 5.06 (s, 3H); 13C NMR (DMSO-d6) δ 160.90, 157.69 (d, J=152.9), 145.58, 144.49 (d, J=5.2), 141.74, 134.57, 134.30, 130.29, 127.14, 126.18, 124.21, 122.41 (d, J=8.2), 122.23 (d, J=9.6), 122.02 (d, J=10.4), 121.85, 116.10, 114.57, 113.51, 106.46 (d, J=26.2), 40.60; MS (EI, m/z) 341 (M+ -H) .

Workup

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

Sources & evidence

ORD record
ord-c2ae3536e260478a96faa526b471aad6
Source dataset
uspto-grants-1999_07
Patent number
US05925647

Reaction notes

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