Hydrazine hydrate (1:1) → HCID 178509230, compound

HRID 1055102Notes

Reaction equation

HRID 1055102 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][C:5]([F:10])=[CH:4][N:3]=1.O.[NH2:12][NH2:13]>C(O)CCC>[F:10][C:5]1[CH:6]=[C:7]2[C:8]([NH2:9])=[N:13][NH:12][C:2]2=[N:3][CH:4]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 231108512-Chloro-5-fluoropyridine-3-carbonitrile2×

Product 1

HCID 178509230HCID 178509230, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

To the mixture of 2-chloro-5-fluoropyridine-3-carbonitrile, 131a, (29.6 g, 157.1 mmol) in n-butanol (492 mL) was added hydrazine hydrate (76.4 mL, 1.6 mol). This mixture was heated to reflux for 4.5 h and cooled down. n-Butanol was removed under reduced pressure and water (300 mL) was added resulting in a yellow precipitate. The suspension was filtered and washed with water twice, followed by a MTBE wash. The yellow solid was dried in a vacuum oven to give 18 g of the desired product: 1H NMR (300 MHz, DMSO-d6) δ 12.08 (s, 1H), 8.38 (dd, J=2.7, 1.9 Hz, 1H), 7.97 (dd, J=8.8, 2.7 Hz, 1H), 5.56 (s, 2H). LCMS Gradient 10-90%, 0.1% formic acid, 5 minutes, C18/ACN, Retention Time=1.25 minutes (M+H) 152.95.

Workup

  1. temperatureThis mixture was heated
  2. temperatureto reflux for 4.5 h
  3. temperaturecooled down
  4. customn-Butanol was removed under reduced pressure and water (300 mL)
  5. additionwas added
  6. customresulting in a yellow precipitate
  7. filtrationThe suspension was filtered
  8. washwashed with water twice
  9. washwash
  10. customThe yellow solid was dried in a vacuum oven

Sources & evidence

ORD record
ord-54b6c103f6774b8390fc4828b508058c
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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