Sodium Hydroxide → HCID 21221573, compound

HRID 1457074Notes

Reaction equation

HRID 1457074 reaction equation
[CH3:1][N:2]([CH3:21])[CH:3]1[CH2:20][CH2:19][C:6]2[O:7][C:8]3[CH:13]=[CH:12][C:11]([C:14]([O:16]CC)=[O:15])=[CH:10][C:9]=3[C:5]=2[CH2:4]1.[OH-].[Na+]>O1CCCC1.Cl>[CH3:1][N:2]([CH3:21])[CH:3]1[CH2:20][CH2:19][C:6]2[O:7][C:8]3[CH:13]=[CH:12][C:11]([C:14]([OH:16])=[O:15])=[CH:10][C:9]=3[C:5]=2[CH2:4]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 21221595HCID 21221595, compound

Product 1

HCID 21221573HCID 21221573, compoundYield 55%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
35 °C

Procedure

A mixture of 0.21 gm (0.73 mMol) N,N-dimethyl-8-ethoxycarbonyl-1,2,3,4-tetrahydro-2-dibenzofuranamine and 25 mL 2N sodium hydroxide in 25 ml tetrahydrofuran was stirred at 35° C. for 18 hours. The reaction mixture was cooled to room temperature and washed with dichlorometh-ane. The aqueous phase was adjusted to pH~7, saturated with sodium chloride, and then extracted well with chloroform containing 10% isopropanol. Organic extracts were combined and concentrated under reduced pressure to provide a white solid which was taken up in hydrochloric acid. The colorless crystalline precipitate which formed was filtered and dried to provide 0.098 ggm (55%) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. washwashed with dichlorometh-ane
  3. extractionextracted well with chloroform containing 10% isopropanol
  4. concentrationconcentrated under reduced pressure
  5. customto provide a white solid which
  6. customThe colorless crystalline precipitate which formed
  7. filtrationwas filtered
  8. customdried

Sources & evidence

ORD record
ord-4c93a4ab006e4e3589158ae5949b17a5
Source dataset
uspto-grants-1998_12
Patent number
US05846995

Reaction notes

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