Water → 3-Methoxy-N2-(2-morpholin-4-ylethyl)benzene-1,2-diamine

HRID 1095385Notes

Reaction equation

HRID 1095385 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-])=O)[C:10]=1[NH:18][C:19](=O)[CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1.O.[OH-].[Na+]>C1COCC1.C(OCC)(=O)C>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([NH2:15])[C:10]=1[NH:18][CH2:19][CH2:20][N:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 57436028N-(2-methoxy-6-nitrophenyl)-2-morpholin-4-ylacetamide

Product 1

HCID 686249603-Methoxy-N2-(2-morpholin-4-ylethyl)benzene-1,2-diamineYield 44%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of lithium aluminum hydride (5.2 g, 136 mmol) in THF (35 mL) was added a solution of N-(2-methoxy-6-nitrophenyl)-2-morpholin-4-ylacetamide (Step 2, 6.7 g, 23 mmol) in THF (40 mL) at 0° C. and stirred at reflux for 2 h. Then to this mixture was added water (5.2 mL) followed by addition of 15% sodium hydroxide (5.2 mL), water (15.6 mL) at 0° C. The mixture was diluted with ethyl acetate (100 mL) and stirred for 3 h at rt. The resultant mixture was filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel eluting with dichloromethane/methanol (30/1) to afford 2.5 g (44%) of the title compound.

Workup

  1. temperatureat reflux for 2 h
  2. stirringstirred for 3 h at rt
  3. filtrationThe resultant mixture was filtered
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel eluting with dichloromethane/methanol (30/1)

Sources & evidence

ORD record
ord-bb4f546590234b77912d2f902166f1f9
Source dataset
uspto-grants-2012_03
Patent number
US08138177B2

Reaction notes

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