Hydrochloric Acid → HCID 57893428, compound

HRID 1822377Notes

Reaction equation

HRID 1822377 reaction equation
[OH:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]([CH2:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4](=[O:22])[C:3]=1[C:23](OCC)=[O:24].[H-].[Na+].OC1C(C2C=CC=CC=2)=NNC(=O)[C:32]=1[C:44]([O:46]CC)=[O:45].ICCC1C=CC=CC=1.Cl.C[N:60](C)C=O>>[OH:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:6][N:5]([CH2:14][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:4](=[O:22])[C:3]=1[C:23]([NH:60][CH2:32][C:44]([OH:46])=[O:45])=[O:24]

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 28503Benzene, (2-iodoethyl)-HCID 68812286HCID 68812286, compoundHCID 68812878HCID 68812878, compound

Product 1

HCID 57893428HCID 57893428, compoundYield 55%

Procedure

Ethyl 5-hydroxy-3-oxo-6-phenyl-2-(2-phenylethyl)-2,3-dihydro-4-pyridazinecarboxylate. Sodium hydride (0.040 g of a 60% oil suspension, 1.00 mmol) was added to a stirred solution of ethyl 5-hydroxy-3-oxo-6-phenyl-2,3-dihydro-4-pyridazinecarboxylate (example 4(b), 0.100 g, 0.384 mmol) in dimethylformamide (1.5 mL) under nitrogen. After 15 min stirring at room temperature, the mixture was cooled in an ice bath and (2-iodoethyl)benzene (0.056 mL, 0.384 mmol) injected. The mixture was stirred for 18 h while warming to room temperature, then poured into 0.1M aqueous hydrochloric acid (50 mL) and extracted with ethyl acetate. The extracts were washed with water and brine, then dried (MgSO4), evaporated under reduced pressure and the residue chromatographed (silica gel, 1-5% methanol dichloromethane) to give the title compound (0.077 g, 55%) as a colourless gum. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.30 (t, J=7.07 Hz, 3H) 3.04 (t, J=7.33 Hz, 2H) 4.30 (t, J=7.32 Hz, 2H) 4.32 (q, J=7.07 Hz, 2H) 7.20-7.26 (m, 3H) 7.28-7.35 (m, 2H) 7.40-7.47 (m, 3H) 7.50-7.56 (m, 2H) 12.45 (br. s., 1 H).

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. stirringThe mixture was stirred for 18 h
  3. temperaturewhile warming to room temperature
  4. extractionextracted with ethyl acetate
  5. washThe extracts were washed with water and brine
  6. dry with materialdried (MgSO4)
  7. customevaporated under reduced pressure
  8. customthe residue chromatographed (silica gel, 1-5% methanol dichloromethane)

Sources & evidence

ORD record
ord-f29a7ce6fa934516b941bc7ed88bfb5a
Source dataset
uspto-grants-2009_10
Patent number
US07608621B2

Reaction notes

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