Phenol → HCID 86751466, compound

HRID 1490282Notes

Reaction equation

HRID 1490282 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-3b5c9f9cb09d477ea26e0143380c0a0e
Source dataset
uspto-grants-1997_10
Patent number
US05681958

Reaction notes

Loading…