Ammonia → HCID 68424460, compound

HRID 1044476Notes

Reaction equation

HRID 1044476 reaction equation
O.Cl.O[C:4]1([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH2:8][CH2:7][C:6]([C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[CH:16][CH:15]=[CH:14]3)=[C:5]1[CH3:19].N>O1CCCC1>[CH3:19][C:5]1[C:4]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[CH:8][CH2:7][C:6]=1[C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[N:17]=[CH:16][CH:15]=[CH:14]2

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 962WaterHCID 68425885HCID 68425885, compound

Product 1

HCID 68424460HCID 68424460, compoundYield 69.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5 ml of water and 5 ml of concentrated hydrochloric acid was added to a solution of 1.717 g (5.7 mmol) of 3-hydroxy-2-methyl-3-phenyl-1-(8-quinolyl)cyclopentene in 100 ml of tetrahydrofuran. The mixture was stirred at room temperature for 90 minutes and ammonia solution was then added until the pH was 12. The aqueous phase was then separated off from the organic phase and the aqueous phase was extracted twice with diethyl ether. The organic phases were combined, dried over magnesium sulfate, filtered and the solvent was distilled off. The residue obtained in this way was distilled at 157-170° C. and 2×10−2 mbar to give 1.12 g (3.95 mmol, 69.3%) of 2-methyl-3-phenyl-1-(8-quinolyl)cyclopentadiene.

Workup

  1. customThe aqueous phase was then separated off from the organic phase
  2. extractionthe aqueous phase was extracted twice with diethyl ether
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. distillationthe solvent was distilled off
  6. customThe residue obtained in this way
  7. distillationwas distilled at 157-170° C.

Sources & evidence

ORD record
ord-74c501c0ebeb42f480c7bb7d550f6ab9
Source dataset
uspto-grants-2013_10
Patent number
US08563674B2

Reaction notes

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