Hydrochloric Acid → HCID 59161291, compound

HRID 545510Notes

Reaction equation

HRID 545510 reaction equation
O=[C:2]1[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])[CH2:4][CH2:3]1.Cl.[O:15]1[C:19]2[CH:20]=[CH:21][C:22]([NH:24]N)=[CH:23][C:18]=2[O:17][CH2:16]1.Cl>O>[O:17]1[C:18]2=[CH:23][C:22]3[NH:24][C:2]4[CH2:7][CH2:6][CH:5]([NH:8][C:9](=[O:13])[CH:10]([CH3:12])[CH3:11])[CH2:4][C:3]=4[C:21]=3[CH:20]=[C:19]2[O:15][CH2:16]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 215339942-Methyl-N-(4-oxocyclohexyl)propanamideHCID 22291622(2H-1,3-Benzodioxol-5-yl)hydrazine--hydrogen chloride (1/1)

Product 1

HCID 59161291HCID 59161291, compoundYield 75.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Add N-(4-oxo-cyclohexyl)-isobutyramide (974 mg, 5.32 mmol) a suspension of benzo[1,3]dioxol-5-yl-hydrazine hydrochloride salt (Clemo, G. R.; Weiss, J. J. Chem. Soc. (1945), 702.) (1.00 g, 5.32 mmol) to water (7 mL) and concentrated hydrochloric acid (3 mL). Heat the reaction to 90° C. for 12 h and cool to ambient temperature. Collect the resultant solid by vacuum filtration, rinse with water and place under high vacuum for 12 h to afford the titled compound (1.20 g, 75%) as a dark brown solid. m.p.=198-200° C.; 1H NMR (300 MHz, CDCl3): δ 7.77 (br s, 1H), 6.81 (s, 1H), 6.78 (s, 1), 5.91 (s, 2H), 5.57 (br s, 1H), 4.40 (br s, 1H), 3.00 (dd, J=15.4, 5.1 Hz, 1H), 2.80-2.69 (m, 2H), 2.50 (dd, J=15.4, 6.5 Hz, 11H), 2.30 (septet, J=6.9 Hz, 1H), 2.05-1.96 (m, 2H), 1.14 (d, J=6.9 Hz, 6H).

Workup

  1. temperatureHeat
  2. customthe reaction to 90° C. for 12 h
  3. customCollect the resultant solid
  4. filtrationby vacuum filtration
  5. washrinse with water and place under high vacuum for 12 h

Sources & evidence

ORD record
ord-8e95e66b1076452c8c077dc8e21395f3
Source dataset
uspto-grants-2011_05
Patent number
US07935722B2

Reaction notes

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