Ammonium Chloride → 3,3-Dimethyl-1-[2-benzylperhydropyridazinyl]pentane-1,2-dione

HRID 851944Notes

Reaction equation

HRID 851944 reaction equation
[O:1]=[C:2]([CH:7]1[CH2:12][CH2:11][CH2:10][NH:9][N:8]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:3]([O:5]C)=O.[CH3:20][C:21]([Mg]Cl)([CH3:24])[CH2:22][CH3:23].[Cl-].[NH4+]>C1COCC1>[CH3:20][C:21]([CH3:24])([CH2:22][CH3:23])[C:3](=[O:5])[C:2]([CH:7]1[CH2:12][CH2:11][CH2:10][NH:9][N:8]1[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:1]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 18470067Methyl 2-oxo-2-[2-benzylperhydropyridazinyl]acetateHCID 178446075HCID 178446075, compound

Product 1

HCID 184700773,3-Dimethyl-1-[2-benzylperhydropyridazinyl]pentane-1,2-dioneYield 69%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 2-oxo-2-[2-benzylperhydropyridazinyl]acetate (9.0 g, 29.4 mmol) in 30 ml dry THF was cooled to −78° C. and treated with 35 ml of 1.0 M solution of 1,1-dimethylpropylmagnesium chloride in THF. After stirring the resulting homogeneous mixture at for 5 hours, the mixture was poured into saturated ammonium chloride (150 ml) and extracted into ethyl acetate. The organic layer was washed with water, dried and concentrated. The crude material was purified by silica gel column, eluting with 10% ethyl acetate in hexane, to obtain 7.0 g product (69% yield) as clear oil. 1H NMR (CDCl3, 400 MHz): δ 0.76 (t, 3H, J=7.0); 1.06 (s, 6H) 1.69 (m, 6H); 2.80 (m, 1H); 3.15 (m, 1H), 4.03 (m, 1H); 4.13 (m, 1H), 5.18 (m, 2H), 7.36 (m, 5H).

Workup

  1. extractionextracted into ethyl acetate
  2. washThe organic layer was washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe crude material was purified by silica gel column
  6. washeluting with 10% ethyl acetate in hexane

Sources & evidence

ORD record
ord-5b7e5302d9f94c2391f5b08c3cbff002
Source dataset
uspto-grants-2007_08
Patent number
US07253169B2

Reaction notes

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