Hydrochloric Acid → HCID 54739144, compound

HRID 1822384Notes

Reaction equation

HRID 1822384 reaction equation
[OH:1][C:2]1[C:7]([CH3:8])=[N:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-:18])=[O:17])[C:4](=[O:19])[C:3]=1[C:20]([O:22]CC)=O.[H-].[Na+].[N+:27](C1C=CC=CC=1CBr)([O-])=O.Cl.CC[O:41][C:42]([CH3:44])=[O:43]>CN(C)C=O.O>[OH:1][C:2]1[C:7]([CH3:8])=[N:6][N:5]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-:18])=[O:17])[C:4](=[O:19])[C:3]=1[C:20]([NH:27][CH2:44][C:42]([OH:41])=[O:43])=[O:22]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 77569alpha-Bromo-2-nitrotolueneHCID 68813731HCID 68813731, compound

Product 1

HCID 54739144HCID 54739144, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Ethyl 5-hydroxy-6-methyl-2-[(2-nitrophenyl)methyl]-3-oxo-2,3-dihydro-4-pyridazinecarboxylate. Sodium hydride (50 mg, 1.26 mmol) was added to a solution of the compound from example 28b) (100 mg, 0.50 mmol) in N,N-Dimethylformamide (DMF) (2 mL) at 0° C. The reaction was brought to room temperature and stirred for 45 minutes. The temperature was then reduced to 0° C. and 2-nitrobenzyl bromide (109 mg, 0.50 mmol) was added. The reaction was brought to room temperature and stirred for 3 hours followed by the addition of 1N HCl. The solution was diluted with EtOAc and H2O and the layers separated. The aqueous layer was backextracted with EtOAc several times. The combined organic layers were washed with Brine, dried (MgSO4), filtered and concentrated. The product was purified by column chromatography (SiO2, 0-6% MeOH/CH2Cl2) to give the title compound as an orange oil (83 mg, 50%). 1H NMR (400 MHz, DMSO-d6) δ ppm 12.28 (s, 1H) 8.08 (dd, J=8.08, 1.26 Hz, 1H) 7.70 (td, J=7.64, 1.39 Hz, 1H) 7.53-7.61 (m, 1H) 7.18 (dd, J=7.71, 0.88 Hz, 1H) 5.45 (s, 2H) 4.26 (q, J=7.24 Hz, 2H) 2.20 (s, 3H) 1.25 (t, J=7.07 Hz, 3H).

Workup

  1. customwas brought to room temperature
  2. customwas then reduced to 0° C.
  3. customwas brought to room temperature
  4. stirringstirred for 3 hours
  5. customthe layers separated
  6. washThe combined organic layers were washed with Brine
  7. dry with materialdried (MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe product was purified by column chromatography (SiO2, 0-6% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-cd2cbc7a05124a49b63bb279c80bd805
Source dataset
uspto-grants-2009_10
Patent number
US07608621B2

Reaction notes

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