Hydrochloric Acid → HCID 67415276, compound

HRID 490847Notes

Reaction equation

HRID 490847 reaction equation
B.[CH3:2][C:3]1[CH:4]=[C:5]([CH:8]=[C:9]([CH3:12])[C:10]=1[OH:11])[C:6]#[N:7].[ClH:13]>O1CCCC1>[ClH:13].[NH2:7][CH2:6][C:5]1[CH:4]=[C:3]([CH3:2])[C:10]([OH:11])=[C:9]([CH3:12])[CH:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 6331BoraneHCID 201763,5-Dimethyl-4-hydroxybenzonitrile

Product 1

HCID 67415276HCID 67415276, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of borane in tetrahydrofuran (27.1 ml of a 1M solution, 27.1 mmol) was added dropwise to a solution of 3,5-dimethyl-4-hydroxybenzonitrile (1.0 g, 6.79 mmol) in tetrahydrofuran (70 ml) and the resulting solution heated to reflux under a nitrogen atmosphere for 16 hours. The reaction was cooled to room temperature and treated with 6N hydrochloric acid (20 ml) and refluxed for a further 30 minutes. The reaction mixture was cooled to room temperature and the solvent removed in vacuo. Purification using strong cation exchange resin, eluting biproducts with methanol followed by 2M ammonia in methanol to elute the product gave the title compound as an orange oil. The oil was treated with 1M hydrogen chrloide in methanol (20 ml) and the solvent removed in vacuo to give the title compound as a pale yellow solid (1.12 g).

Workup

  1. temperaturethe resulting solution heated
  2. temperatureto reflux under a nitrogen atmosphere for 16 hours
  3. temperaturerefluxed for a further 30 minutes
  4. temperatureThe reaction mixture was cooled to room temperature
  5. customthe solvent removed in vacuo
  6. customPurification
  7. washeluting biproducts with methanol
  8. washto elute the product

Sources & evidence

ORD record
ord-e2c371d2330345838f4390c8e8c793f6
Source dataset
uspto-grants-2009_05
Patent number
US07528170B2

Reaction notes

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