HCID 86625749, compound → HCID 86625748, compound

HRID 1158618Notes

Reaction equation

HRID 1158618 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:5]=[C:4]([O:14][CH3:15])[C:3]=1[N+:16]([O-])=O>Cl>[Cl:1][C:2]1[C:3]([NH2:16])=[C:4]([O:14][CH3:15])[CH:5]=[C:6]([N:8]2[CH2:9][CH2:10][O:11][CH2:12][CH2:13]2)[N:7]=1

Participants

3

Reactant 1

HCID 86625749HCID 86625749, compound

Product 1

HCID 86625748HCID 86625748, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Conditions

Temperature
75 °C

Procedure

To a solution of 4-(6-chloro-4-methoxy-5-nitropyridin-2-yl)-morpholine (0.38 g) in concentrated hydrochloric acid (20 mL) was added a solution of stannous dichloride (1.57 g) in concentrated hydrochloric acid (60 mL). The reaction mixture was heated to 75° C. for 5 minutes and then poured on to chrushed ice (100 g) and extracted with ethyl acetate (2×20 mL). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo, to furnish 0.28 g (83% yield) of the title compound as an off-white solid. 1H NMR (500 MHz, CDCl3): 3.35 (m, 4H), 3.65 (br s, 2H), 3.80 (m, 4H), 3.90 (s, 3H), 6.10 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1fd87eb574d48ceac36e90293af802f
Source dataset
uspto-grants-2010_10
Patent number
US07812020B2

Reaction notes

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