Ammonium Hydroxide → HCID 57718257, compound

HRID 1366862Notes

Reaction equation

HRID 1366862 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][C:5](Cl)=[CH:6][C:7]=1[CH2:8][CH2:9][CH2:10][CH3:11].[OH-].[NH4+:14]>C(O)C>[NH2:14][C:5]1[N:4]=[N:3][C:2]([Cl:1])=[C:7]([CH2:8][CH2:9][CH2:10][CH3:11])[CH:6]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 15851832HCID 15851832, compound

Product 1

HCID 57718257HCID 57718257, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3,6-dichloro-4-n-butylpyridazine (7.1 g, 34 mmol), ethanol (70 ml) and 25% aqueous ammonium hydroxide (70 ml) was heated to 135 deg in a sealed pressure resistant reaction vessel (Parr: achieving a pressure of 90 psi) for 24 hours. After this time the mixture was cooled and concentrated under reduced pressure. The residue was partitioned between dichloromethane (250 ml) and water (250 ml) and the aqueous layer re -extracted with dichloromethane (200 ml). The combined organic extracts were dried over magnesium sulfate and concentrated under reduced pressure to give the crude product as a mixture of isomers. Purification by flash chromotography (10-100% ethyl acetate/hexane) gave 3-amino-5-n-butyl-6-chloropyridazine as a white solid (2.3 g, 36%). 1H-NMR (CDCl3) 6.55 (1H, s, 4-H), 4.98 (2H, bs, NH2), 2.57 (2H, t, Bu), 1.58 (2H, m, Bu), 1.37 (2H, m, Bu), 0.91 (3H, t, Bu)

Workup

  1. temperaturewas heated to 135 deg in a sealed pressure resistant reaction vessel (Parr
  2. customfor 24 hours
  3. temperatureAfter this time the mixture was cooled
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between dichloromethane (250 ml) and water (250 ml)
  6. dry with materialThe combined organic extracts were dried over magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customto give the crude product
  9. additionas a mixture of isomers
  10. customPurification by flash chromotography (10-100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-edadc7cf14714d8fbf0f3da5f6f11caf
Source dataset
uspto-grants-2011_02
Patent number
US07893077B2

Reaction notes

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