Pyridine → HCID 14497416, compound

HRID 373486Notes

Reaction equation

HRID 373486 reaction equation
Cl.[CH3:2][O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][NH2:11])=[CH:6][CH:5]=1.N1C=CC=CC=1.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([C:25](=O)[CH2:26][C:27](=O)[CH2:28][CH2:29][CH2:30][OH:31])=[CH:21][CH:20]=1>CO>[Cl:18][C:19]1[CH:20]=[CH:21][C:22]([C:25]2[N:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][CH3:2])=[CH:5][CH:6]=3)[N:11]=[C:27]([CH2:28][CH2:29][CH2:30][OH:31])[CH:26]=2)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27239044-Methoxyphenylhydrazine hydrochlorideHCID 144974141-(4-Chlorophenyl)-6-hydroxyhexan-1,3-dione

Product 1

HCID 14497416HCID 14497416, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent3×

Procedure

4-Methoxyphenylhydrazine hydrochloride [35.0 grams (g), 0.20 moles] was added to CH3OH [50 milliliters (ml)] containing pyridine (20 ml). An additional amount of CH3OH (25 ml) was added to the thick resulting slurry. 1-(4-Chlorophenyl)-6-hydroxyhexan-1,3-dione (48.2 g, 0.20 moles), was added neat, followed by more CH3OH (25 ml). The slurry was stirred at room-temperature for 1.5 hours, after which time the mixture was concentrated and taken up in CHCl3 (300 ml). The CHCl3 solution was washed with 1N HCl (300 ml), dried (Na2SO4), filtered, and concentrated. The oil was decolorized (Norit) in hot diethyl ether (Et2O) (300 ml). The Et2O solution was cooled, and crystallization from Et2O (300 ml) afforded 2 (49.4 g). From the filtrate was obtained additional 2 (9.28 g), total yield 91%, mp 87.5°-88°. NMR (CDCl3) 1.7-2.3 (m, 2H, CH2CH2CH2), 2.55 (brs, 1H, OH), 2.80 (t, 2H, J=7 Hz, CH2), 3.75 (t, 2H, J=6 Hz, CH2O), 3.77 (s, 3H, OCH3), 6.28 (s, 1H, C4 -H), 6.93 (ABq, 4 H, J=12, 9, 4-OMe-C6H4), 6.9-7.3 (m, 4H, 4-Cl--C6H4); IR (KBr) 3320, 2920, 1495; MS, m/e 342 (M+), 312, 298 (100%);

Workup

  1. concentrationafter which time the mixture was concentrated
  2. washThe CHCl3 solution was washed with 1N HCl (300 ml)
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. temperatureThe Et2O solution was cooled
  7. customcrystallization from Et2O (300 ml)

Sources & evidence

ORD record
ord-30be77d51e0849259d461c3807bbb817
Source dataset
uspto-grants-1992_11
Patent number
US05164381

Reaction notes

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