Hydroxide → HCID 22040275, compound

HRID 343891Notes

Reaction equation

HRID 343891 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[OH:9].[OH-:10].C[CH:12]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22](Cl)=[O:23])[C:13](Cl)=[O:14].[OH-].[Na+]>O1CCCC1.O>[OH:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[NH:1][C:22]([CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:12][C:13]([OH:14])=[O:10])=[O:23]

Participants

7

Reactant 4

HCID 961HydroxideHCID 72652-Amino-4-chlorophenolHCID 14798Sodium HydroxideHCID 22251413HCID 22251413, compound

Product 1

HCID 22040275HCID 22040275, compoundYield 54.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a cold solution of 2-amino-4-chlorophenol (2.56 g, 17.83 mmol) in tetrahydrofuran (40 mL) was added a solution of hydroxide (0.72 g, 18 mmol) in water (15 mL). The mixture was stirred at 0° C. for 5 min. A solution of methyl azeloyl chloride (3.9 g, 17.67 mmol) in tetrohydrofuran (10 mL) was added dropwise to this mixture. The resulting mixture was stirred at 0° C., then gradually warmed to room temperature, and stirred at room temperature overnight. A solution of sodium hydroxide (2N, 25 mL) was added to the reaction mixture. The mixture was stirred at room temperature and monitored by TLC. When the starting material was no longer visible, the reaction mixture was concentrated in vacuo. The residue was acidified to pH 2, and the precipitated solid was collected by filtration. This crude product was dissolved in methanol (50 mL), decolorized with activated charcoal, and filtered. A small amount of acetone and water was added to the filtrate, and the mixture refrigerated overnight. A solid was formed, collected by filtration, washed with water, and dried to give the product as a pale yellow, crystalline solid (3.0 g, 54%); mp 117°-118° C.; 1H NMR (DMSO-d6) δ7.96 (d. J=2.5 Hz, 1H), 6.95 (dd, J=8.6, 2.6 Hz, 1H), 6.85 Hz, 1H), 2.39 (t, J=7.3 Hz, 2H), 2.19 (t, J=7.3 Hz, 2H), 1.40-1,61 (m, 4H), 1.20-1.35 (m, 6H). Anal. Calcd for C5H20CINO4 :C, 57.42; H, 6.42; N, 4.46. Found: C, 57.24; H, 6.30; N, 4.41.

Workup

  1. stirringThe resulting mixture was stirred at 0° C.
  2. temperaturegradually warmed to room temperature
  3. stirringstirred at room temperature overnight
  4. stirringThe mixture was stirred at room temperature
  5. concentrationthe reaction mixture was concentrated in vacuo
  6. filtrationthe precipitated solid was collected by filtration
  7. dissolutionThis crude product was dissolved in methanol (50 mL)
  8. filtrationfiltered
  9. additionA small amount of acetone and water was added to the filtrate
  10. customthe mixture refrigerated overnight
  11. customA solid was formed
  12. filtrationcollected by filtration
  13. washwashed with water
  14. customdried

Sources & evidence

ORD record
ord-e626464f639f48bfb154630777d1b61b
Source dataset
uspto-grants-1999_01
Patent number
US05863944

Reaction notes

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