Acetic Acid → 3-Methyl-6-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)-phenoxy]-propyl]-pyridazine

HRID 1377830Notes

Reaction equation

HRID 1377830 reaction equation
[CH3:1][C:2]1(OC)O[C:5]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([C:20]3[N:21]=[N:22][N:23]([CH3:25])[N:24]=3)=[CH:15][C:14]=2[CH3:26])(OC)[CH:4]=[CH:3]1.CO.C(O)(=O)C.O.[NH2:36][NH2:37]>O>[CH3:1][C:2]1[N:36]=[N:37][C:5]([CH2:9][CH2:10][CH2:11][O:12][C:13]2[C:18]([CH3:19])=[CH:17][C:16]([C:20]3[N:21]=[N:22][N:23]([CH3:25])[N:24]=3)=[CH:15][C:14]=2[CH3:26])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 24654Hydrazine hydrate (1:1)HCID 229153545-Methyl-2-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)phenoxy]-propyl]-2,5-dimethoxy-2,5-dihydrofuran

Product 1

HCID 159546423-Methyl-6-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)-phenoxy]-propyl]-pyridazineYield 29%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under nitrogen with stirring 5-methyl-2-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)phenoxy]-propyl]-2,5-dimethoxy-2,5-dihydrofuran (820 mg, 1.8 mmol), 0.8 mL of methanol, and 1.5 mL of 1% aqueous acetic acid solution were combined at room temperature, refluxed for 10 min, and then cooled to room temperature. To the above solution was added hydrazine hydrate (0.26 mL) over a 2 min period, and the mixture was allowed to reflux for 1 h, and cooled to room temperature. The mixture was diluted with water, the aqueous layer was extracted with methylene chloride, and the organic layer was washed with brine, dried over magnesium sulfate, and concentrated in vacuo to afford 180 mg (29%) of 3-methyl-6-[3-[2,6-dimethyl-4-(2-methyl-tetrazol-5-yl)-phenoxy]-propyl]-pyridazine (Formula I; R1, R2 =3,5-dimethyl, R3 =6-methyl, R4 =hydrogen, R5 =2-methyltetrazol-5-yl), m.p. 114°-115° C.

Workup

  1. customwere combined at room temperature
  2. temperaturerefluxed for 10 min
  3. temperatureto reflux for 1 h
  4. temperaturecooled to room temperature
  5. extractionthe aqueous layer was extracted with methylene chloride
  6. washthe organic layer was washed with brine
  7. dry with materialdried over magnesium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-de0402def180493bba9f089f12f5f544
Source dataset
uspto-grants-1997_09
Patent number
US05665763

Reaction notes

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