Hydrazine hydrate (1:1) → HCID 90410181, compound

HRID 869120Notes

Reaction equation

HRID 869120 reaction equation
[NH2:1][C:2](C(Cl)(Cl)Cl)=[C:3]([C:15]#[N:16])[C:4]([NH:6][C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[O:13][CH3:14])=O.[OH2:21].[NH2:22][NH2:23]>CN1CCCC1=O>[NH2:1][C:2]1[C:3]([C:4]([NH:6][C:7]2[CH:8]=[N:9][CH:10]=[CH:11][C:12]=2[O:13][CH3:14])=[O:21])=[C:15]([NH2:16])[NH:23][N:22]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 131732526HCID 131732526, compound

Product 1

HCID 90410181HCID 90410181, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

3-Amino-4,4,4-trichloro-2-cyano-N-(4-methoxy-3-pyridyl)but-2-enamide (37.2 g, 110.9 mmol) was dissolved in N-methylpyrrolidinone (200 mL). Hydrazine hydrate (14.43 g, 14.02 mL, 288.3 mmol) was added portionwise, then the mixture heated to 80° C. for 20 hr. The mixture was cooled to ambient and concentrated in vacuo. The viscous red oil was stirred as TBME (180 ml)/DCM (20 ml) was added. The yellow solid that precipitated was filtered, washed with TBME and dried to afford the title compound (26.9 g, 98%). LC-MS (M+H)+ 249.0; 1H NMR (500 MHz, DMSO-d6) δ 11.90 (br s, 1H), 9.32 (s, 1H), 9.14 (s, 1H), 8.15 (d, 1H), 7.10 (d, 1H), 3.92 (s, 3H).

Workup

  1. temperatureThe mixture was cooled to ambient and
  2. concentrationconcentrated in vacuo
  3. additionwas added
  4. filtrationThe yellow solid that precipitated was filtered
  5. washwashed with TBME
  6. customdried

Sources & evidence

ORD record
ord-0b8a6a778ef941fc83f796220e5a7244
Source dataset
uspto-grants-2015_03
Patent number
US08969360B2

Reaction notes

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