HCID 66862671, compound → HCID 66861383, compound

HRID 1158617Notes

Reaction equation

HRID 1158617 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-])=O)=[C:6]([O:11][CH3:12])[N:5]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:3]=1>Cl>[Cl:1][C:2]1[CH:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[N:5]=[C:6]([O:11][CH3:12])[C:7]=1[NH2:8]

Participants

3

Reactant 1

HCID 66862671HCID 66862671, compound

Product 1

HCID 66861383HCID 66861383, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent2×

Conditions

Temperature
75 °C

Procedure

To a solution of 4-(4-chloro-6-methoxy-5-nitropyridin-2-yl)-morpholine (0.82 g) in concentrated hydrochloric acid (50 mL) was added a solution of stannous dichloride (3.38 g) in concentrated hydrochloric acid (80 mL). The reaction mixture was heated to 75° C. for 1 hour and then poured on to chrushed ice (400 g) and extracted with ethyl acetate (2×100 mL). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo, to furnish 0.45 g (61% yield) of the title compound as an off-white solid. LC-MS (m/z) 244 (M+); tR=1.48, (UV, ELSD) 89%, 94%. 1H NMR (500 MHz, CDCl3): 3.30 (m, 4H), 3.65 (br s, 2H), 3.85 (m, 4H), 3.97 (s, 3H), 6.20 (s, 1H).

Workup

  1. extractionextracted with ethyl acetate (2×100 mL)
  2. dry with materialThe combined organic phases were dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-dbf3c76a3739477d87ea2ae6895ac817
Source dataset
uspto-grants-2010_10
Patent number
US07812020B2

Reaction notes

Loading…