Sodium Nitrite → HCID 86640694, compound

HRID 2176114Notes

Reaction equation

HRID 2176114 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11]2[CH:16]=[CH:15][C:14]([CH3:17])=[CH:13][CH:12]=2)=[CH:4][CH:3]=1.[N:18]([O-])=[O:19].[Na+]>Cl.C(O)C.O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([C:11]2[CH:12]=[CH:13][C:14]([CH3:17])=[CH:15][CH:16]=2)[N:18]=[O:19])=[CH:4][CH:3]=1

Participants

6

Reactant 2

HCID 23668193Sodium NitriteHCID 86640693HCID 86640693, compound

Product 1

HCID 86640694HCID 86640694, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A 250 mL reaction flask was charged with N-(2-(6-chloropyridin-3-yl)ethyl)-4-methylaniline (5 g, 20.3 mmol; Example 117B) in 1 N HCl (22 mL) and ethanol (20 mL). The mixture was stirred at room temperature until complete dissolution was obtained (˜2 hours). The reaction then was cooled in an ice bath and a solution of sodium nitrite (1.55 g, 22.47 mmol; Aldrich) in water (10 mL) was added dropwise with stirring. After the addition was complete, the reaction mixture was allowed to warm briefly to room temperature, then it was cooled again in an ice bath before filtering. The filter cake was washed with water several times and then dried to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 2.38 (s, 3H), 2.88 (t, J=7 Hz, 1H), 4.34 (t, J=7 Hz 2H), 7.25-7.39 (m, 5H), 7.63 (dd, J=8, 2 Hz, 1H), 8.11 (d, J=2 Hz, 1H); MS (DCI/NH3) m/z 276 (M+H)+.

Workup

  1. customA 250 mL reaction flask
  2. customwas obtained (˜2 hours)
  3. customThe reaction
  4. temperaturethen was cooled in an ice bath
  5. stirringwith stirring
  6. additionAfter the addition
  7. temperatureto warm briefly to room temperature
  8. temperatureit was cooled again in an ice bath
  9. filtrationbefore filtering
  10. washThe filter cake was washed with water several times
  11. customdried

Sources & evidence

ORD record
ord-95187489b641403eb97a3bc908d45529
Source dataset
uspto-grants-2015_06
Patent number
US09063126B2

Reaction notes

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