Hydrochloric Acid → HCID 67415276, compound

HRID 1295904Notes

Reaction equation

HRID 1295904 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-36bcca9742704590925b08889a99b812
Source dataset
uspto-grants-2007_07
Patent number
US07244766B2

Reaction notes

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