Toluene → HCID 3635836, compound

HRID 1532651Notes

Reaction equation

HRID 1532651 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1.Cl[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[N+:18]([O-:20])=[O:19].C1(C)C=CC=CC=1>N1C=CC=CC=1>[O:8]1[CH2:9][CH2:10][N:5]([CH2:4][CH2:3][CH2:2][NH:1][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[N+:18]([O-:20])=[O:19])[CH2:6][CH2:7]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 69451-Chloro-2-nitrobenzeneHCID 61055N-(3-Aminopropyl)morpholine

Product 1

HCID 3635836HCID 3635836, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
130 °C

Procedure

N-(3-Aminopropyl)morpholine (1.04 ml) was added to a solution containing 2-chloronitrobenzene (1.005 g) in pyridine (0.78 ml), and stirred for 14 hours at 130° C. Toluene was added to the reaction mixture and concentrated. The residue, with ethyl acetate added thereto, was extracted with 1N hydrochloric acid aqueous solution. The extract was alkalified with 1N sodium hydroxide aqueous solution and extracted with ethyl acetate. The extract was washed with saturated brine, dried over sodium sulfate anhydride, and concentrated, thereby yielding the entitled compound (1.217 g) as orange oil.

Workup

  1. concentrationconcentrated
  2. additionThe residue, with ethyl acetate added
  3. extractionwas extracted with 1N hydrochloric acid aqueous solution
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over sodium sulfate anhydride
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-f1b70ab4fa164e28be5f6a784ebfd0fa
Source dataset
uspto-grants-2001_03
Patent number
US06204264B1

Reaction notes

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