Tert-Butyl nitrite → HCID 67144539, compound

HRID 1848955Notes

Reaction equation

HRID 1848955 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=2[O:16]C)[C:5](N)=[N:6][CH:7]=1.N(OC(C)(C)C)=O>C(O)(=O)C.C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9]3[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:10]=3[O:16][C:5]2=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 10906Tert-Butyl nitriteHCID 64136414HCID 64136414, compound

Product 1

HCID 67144539HCID 67144539, compoundYield 63.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Solution of 5-chloro-3-(5-chloro-2-methoxyphenyl)pyridin-2-amine (5.2 g, 19.3 mmol) in 50 mL of glacial acetic acid and 20 mL of THF was cooled down to -10° C. and tert-butyl nitrite (4.6 mL) was added dropwise. The reaction mixture was stirred overnight at 0° C., warmed to room temperature, diluted with 100 mL of water. Solid material was filtered and dried, providing 2.9 g of pure 3,6-dichlorobenzofuro[2,3-b]pyridine.

Workup

  1. temperaturewarmed to room temperature
  2. filtrationSolid material was filtered
  3. customdried

Sources & evidence

ORD record
ord-3b45e09dc2834c1aa5da100f65fcc199
Source dataset
uspto-grants-2015_02
Patent number
US08952363B2

Reaction notes

Loading…