Ammonium Hydroxide → HCID 57718257, compound

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)

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. extractionthe aqueous layer re-extracted with dichloromethane (200 ml)
7. dry with materialThe combined organic extracts were dried over magnesium sulfate
8. concentrationconcentrated under reduced pressure
9. customto give the crude product
10. additionas a mixture of isomers
11. customPurification by flash chromotography (10-100% ethyl acetate/hexane)

ORD record

ord-4da212a163fd4850b12bfe0bdc650a00

Source dataset

uspto-grants-2009_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07544702B2