Hydrochloric Acid → HCID 57893428, compound

HRID 2046250Notes

Reaction equation

HRID 2046250 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-093a8dc4ed0e44da8ed639c0c699e8ca
Source dataset
uspto-grants-2013_11
Patent number
USRE044613E1

Reaction notes

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