Hydrochloric Acid → 5-hydroxy-5-(3H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

HRID 1095453Notes

Reaction equation

HRID 1095453 reaction equation
Cl.[OH:2][C:3]1([C:15]2[N:16]=[CH:17][N:18](C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:19]=2)[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([C:13]#[N:14])[CH:6]=[CH:5][C:4]1=2>O1CCCC1>[OH:2][C:3]1([C:15]2[NH:16][CH:17]=[N:18][CH:19]=2)[CH2:12][CH2:11][CH2:10][C:9]2[CH:8]=[C:7]([C:13]#[N:14])[CH:6]=[CH:5][C:4]1=2

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 667819655-hydroxy-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Product 1

HCID 667822465-hydroxy-5-(3H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3 ml of 2M HCl are added to a solution of 1 mmol of 5-hydroxy-5-(1-trityl-1H-imidazol-4-yl)-5,6,7,8-tetrahydronaphthalene-2-carbonitrile (Example 1d1) in 15 ml of tetrahydrofuran, and the mixture is heated to reflux for 2 hours. The reaction mixture is cooled to room temperature and evaporated. The residue is mixed with 1M sodium bicarbonate solution and extracted with dichloromethane. The combined organic phases are dried with sodium sulphate and evaporated. The title compound is identified from the residue on the basis of the Rf by flash chromatography (SiO2 60F).

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 2 hours
  3. customevaporated
  4. additionThe residue is mixed with 1M sodium bicarbonate solution
  5. extractionextracted with dichloromethane
  6. dry with materialThe combined organic phases are dried with sodium sulphate
  7. customevaporated

Sources & evidence

ORD record
ord-d1b14651e22b4c14b635a009db986993
Source dataset
uspto-grants-2012_03
Patent number
US08138179B2

Reaction notes

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