Hydrochloric Acid → HCID 57893424, compound

HRID 2046252Notes

Reaction equation

HRID 2046252 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:14](=[O:15])[C:13]([C:16](OCC)=[O:17])=[C:12]([OH:21])[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:10]1.[H-].[Na+].OC1C(C2C=CC=CC=2)=NNC(=O)[C:32]=1[C:44]([O:46]CC)=[O:45].ClC1C=CC=CC=1CBr.Cl.C[N:60](C)C=O>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][N:9]1[C:14](=[O:15])[C:13]([C:16]([NH:60][CH2:32][C:44]([OH:46])=[O:45])=[O:17])=[C:12]([OH:21])[C:11]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:10]1

Participants

7

Reactant 6

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 11905alpha-Bromo-o-chlorotolueneHCID 24758Sodium hydrideHCID 68812286HCID 68812286, compoundHCID 68812883HCID 68812883, compound

Product 1

HCID 57893424HCID 57893424, compoundYield 66%

Procedure

Ethyl 2-[(2-chlorophenyl)methyl]-5-hydroxy-3-oxo-6-phenyl-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-chlorobenzyl bromide (0.051 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 (0.098 g, 66%) as a colourless gum. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.50 (t, J=7.20 Hz, 3H) 4.55 (q, J=7.07 Hz, 2H) 5.54 (s, 2 H) 7.20-7.28 (m, 3H) 7.35-7.52 (m, 4H) 7.75-7.84 (m, 2H) 13.83 (s, 1H).

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-f99e8c9a733f4ea0810be5d93624cdd5
Source dataset
uspto-grants-2013_11
Patent number
USRE044613E1

Reaction notes

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