Acetic Acid → 908608-00-4

HRID 1158613Notes

Reaction equation

HRID 1158613 reaction equation
C(O)(=O)C.[CH3:5][C:6]1[C:11]([N+:12]([O-])=O)=[C:10]([CH3:15])[N:9]=[C:8]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[CH:7]=1>O1CCCC1.[Zn]>[CH3:15][C:10]1[C:11]([NH2:12])=[C:6]([CH3:5])[CH:7]=[C:8]([N:16]2[CH2:17][CH2:18][O:19][CH2:20][CH2:21]2)[N:9]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 66862724HCID 66862724, compound

Product 1

HCID 66862754908608-00-4Yield 100.2%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Glacial acetic acid (25 mL) was added slowly to a mixture of zinc dust (2.76 g) and 4-(4,6-dimethyl-5-nitro-pyridin-2-yl)-morpholine (2.01 g) in tetrahydrofuran (100 mL) cooled to 0° C. The reaction mixture was then stirred for 16 hours at 25° C., filtered through celite, made basic with 25% aqueous ammonia and extracted with tetrahydrofuran (3×75 mL). The combined organic phases were dried over magnesium sulfate and concentrated in vacuo to furnish 1.76 g (100%) of the title compound as a dark red solid. GC-MS (m/z) 207 (M+); tR=7.27. 1H NMR (500 MHz, DMSO-d6): 2.07 (s, 3H), 2.20 (s, 3H), 3.16 (m, 4H), 3.67 (m, 4H), 4.10 (b, 2H), 6.38 (s, 1H).

Workup

  1. filtrationfiltered through celite
  2. extractionextracted with tetrahydrofuran (3×75 mL)
  3. dry with materialThe combined organic phases were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4da80672bd754f2082fe936b435eeed7
Source dataset
uspto-grants-2010_10
Patent number
US07812020B2

Reaction notes

Loading…