Acetone → HCID 90461398, compound

HRID 2202094Notes

Reaction equation

HRID 2202094 reaction equation
Cl.[NH:2]([C:4]1[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=1)[NH2:3].CN(C)/[CH:14]=[CH:15]/[C:16](=O)[CH:17](OC)[O:18]C.CC(=O)C.Cl>C(O)C>[CH:17]([C:16]1[N:2]([C:4]2[CH:11]=[CH:10][C:7]([C:8]#[N:9])=[CH:6][CH:5]=2)[N:3]=[CH:14][CH:15]=1)=[O:18]

Participants

6

Reactant 4

HCID 180AcetoneHCID 313Hydrochloric AcidHCID 5709580((1E)-4,4-dimethoxy-3-oxobut-1-en-1-yl)dimethylamineHCID 162129624-Cyanophenylhydrazine Hydrochloride

Product 1

HCID 90461398HCID 90461398, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-hydrazinylbenzonitrile hydrochloride (10.14 g, 59.78 mmol, 1.00 equiv), (E)-4-(dimethylamino)-1,1-dimethoxybut-3-en-2-one (17.6 g, 101.61 mmol, 1.70 equiv), propan-2-one (30 mL) and 6N hydrochloric acid (30 mL) in ethanol (300 mL) was stirred at 78° C. for 3.5 h. The resulting mixture was cooled to room temperature and concentrated under vacuum. Water (300 mL) and ethyl acetate (200 mL) were added to dissolve the residue. The resulting mixture was extracted with ethyl acetate (2×200 mL). The combined organic layers was washed with water (1×100 mL) and brine (1×100 mL), dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was purified on a silica gel column eluted with 0-20% of ethyl acetate in petroleum ether to give 4 g (34%) of 4-(5-formyl-1H-pyrazol-1-yl)benzonitrile as a yellow solid. 1H-NMR (300 MHz, CDCl3): δ 9.87 (s, 1H), 8.09-7.98 (m, 3H), 7.85-7.83 (m, 2H), 7.36 (d, J=1.5 Hz, 1H) ppm. LCMS (method A, ESI): RT=1.28 min, m/z=198.0 [M+H]+.

Workup

  1. concentrationconcentrated under vacuum
  2. additionWater (300 mL) and ethyl acetate (200 mL) were added
  3. dissolutionto dissolve the residue
  4. extractionThe resulting mixture was extracted with ethyl acetate (2×200 mL)
  5. washThe combined organic layers was washed with water (1×100 mL) and brine (1×100 mL)
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue was purified on a silica gel column
  9. washeluted with 0-20% of ethyl acetate in petroleum ether

Sources & evidence

ORD record
ord-ba0a06a0f99b46ce9ccbcce952fada34
Source dataset
uspto-grants-2016_06
Patent number
US09365527B2

Reaction notes

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