HCID 21963685, compound → HCID 16640415, compound

HRID 2211850Notes

Reaction equation

HRID 2211850 reaction equation
[CH2:1]([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[C:15]1[CH:20]=[CH:19][C:18](Cl)=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N([O-])=[O:23].[Na+].OS([O-])=O.[Na+]>Cl.O>[CH2:1]([N:8]1[CH2:13][CH:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[C:15]1[CH:20]=[CH:19][C:18]([OH:23])=[CH:17][CH:16]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 21963685HCID 21963685, compoundHCID 23665763Sodium BisulfiteHCID 23668193Sodium Nitrite

Product 1

HCID 16640415HCID 16640415, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 1.17 g (122) in 17 mL concentrated HCl: 0.35 g NaNO2 in 5 mL water were added slowly dropwise, so that the temperature remained below 5° C. The solution was agitated for 2 hours at 60° C., neutralized with NaHSO3 and extracted with ether (4×50 mL). The combined organic phases were dried with Na2SO4, evaporated and distilled in a bulb tube (Kp: 0.05 mbar; 140° C.): 0.1 g (123) (123) as colorless oil. DC: CHCl3/methanol (9:1).

Workup

  1. customremained below 5° C
  2. extractionextracted with ether (4×50 mL)
  3. dry with materialThe combined organic phases were dried with Na2SO4
  4. customevaporated
  5. distillationdistilled in a bulb tube (Kp: 0.05 mbar; 140° C.)

Sources & evidence

ORD record
ord-0aeaf62aa324450e96101334ca4f3c2c
Source dataset
uspto-grants-2006_09
Patent number
US07101890B2

Reaction notes

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