Sodium Hydroxide → 3-(Morpholine-4-carbonyl)aniline

HRID 1487145Notes

Reaction equation

HRID 1487145 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[CH:10]=2)=[O:8])[CH2:3][CH2:2]1.[Sn](Cl)Cl.[OH-].[Na+]>C(OCC)(=O)C>[NH2:15][C:11]1[CH:10]=[C:9]([C:7]([N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[O:8])[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24479Stannous ChlorideHCID 225453Morpholino(3-nitrophenyl)methanone

Product 1

HCID 64850643-(Morpholine-4-carbonyl)anilineYield 80.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of morpholino(3-nitrophenyl)methanone (2 g, 8.47 mmol) in Ethyl acetate (40 ml) was added tin(II) chloride dehydrate (7.64 g, 33.9 mmol). Resulting reaction mixture was stirred at RT for 17 h. The reaction mixture was neutralized with NaOH (2N), the mixture was filtered and the filtrate was extracted with Ethyl acetate (250 ml×2). The combined organic layer was washed with brine, dried over sodium sulphate and concentrated under vacuum to give the title product (1.4 g).

Workup

  1. customResulting
  2. customreaction mixture
  3. filtrationthe mixture was filtered
  4. extractionthe filtrate was extracted with Ethyl acetate (250 ml×2)
  5. washThe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulphate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ce06f43d76a74cba90d1a25147bafd56
Source dataset
uspto-grants-2016_08
Patent number
US09428499B2

Reaction notes

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