Acetic Acid → HCID 19595141, compound

HRID 612465Notes

Reaction equation

HRID 612465 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:10][CH2:11][N:12]([C:14]2C=CN=CC=2)[NH2:13])[CH:5]=[C:6](OC)[CH:7]=1.C[O:21][CH2:22]Cl.[OH-].[Na+].[C:26](O)(=O)[CH3:27]>>[F:1][C:2]1[CH:3]=[C:4]2[C:5](=[CH:6][C:7]=1[O:21][CH3:22])[CH2:14][N:12]([NH:13][C:27]1[CH:26]=[CH:14][N:12]=[CH:11][CH:10]=1)[CH2:11][CH2:10]2

Participants

5

Reactant 4

HCID 176Acetic AcidHCID 7864Chloromethyl Methyl EtherHCID 14798Sodium HydroxideHCID 19595301HCID 19595301, compound

Product 1

HCID 19595141HCID 19595141, compoundYield 23%

Conditions

Temperature
0 °C

Procedure

Lithium aluminum hydride (4.5 g) was added portionwise to a suspension of the N-[2-(3-fluoro-5-methoxyphenyl)ethylidine]-N'-4-hydrazine hydrochloride (16.8 g) in tetrahydrofuran (300 ml) at 0° C. The reaction mixture was stirred at ambient temperature for 1 hr, and sodium sulfate decahydrate was added. The mixture was filtered and was concentrated to provide 15.1 g of N-[2-(3-fluoro-5-methoxyphenyl)ethyl]-N-pyridin-4-yl hydrazine. A solution of N-[2-(3-fluoro-5-methoxyphenyl)ethyl]-N-pyridin-4-yl hydrazine (15.1 g) and chloromethyl methyl ether (5.3 g) in acetic acid (240 ml) was heated under reflux for 2 hrs and then cooled to 0° C. 50% Sodium hydroxide solution was added, and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with water and brine, dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated. The residue was recrystallized from methanol to provide 3.5 g (23%) of product, mp 216-218° C.

Workup

  1. temperatureunder reflux for 2 hrs
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe combined organic extracts were washed with water and brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated
  7. customThe residue was recrystallized from methanol

Sources & evidence

ORD record
ord-c0738afd8d544f98ad022c6e81451365
Source dataset
uspto-grants-1999_12
Patent number
US06004977

Reaction notes

Loading…