ethyl N-(3-methoxy-2-nitrophenyl)carbamate → 3-methoxy-N1-methylbenzene-1,2-diamine

HRID 636463Notes

Reaction equation

HRID 636463 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[C:10]([N+:21]([O-])=O)=[C:11]([NH:15][C:16](=O)OCC)[CH:12]=[CH:13][CH:14]=1>O1CCCC1>[NH2:21][C:10]1[C:9]([O:8][CH3:7])=[CH:14][CH:13]=[CH:12][C:11]=1[NH:15][CH3:16]

Participants

4

Reactant 2

HCID 10537989ethyl N-(3-methoxy-2-nitrophenyl)carbamateHCID 21226445Aluminium lithium hydride

Product 1

HCID 106069363-methoxy-N1-methylbenzene-1,2-diamineYield 15.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of lithium aluminum hydride (2.27 g) in tetrahydrofuran (50 ml) was added a suspension of ethyl N-(3-methoxy-2-nitrophenyl)carbamate (7.17 g) in tetrahydrofuran (15 ml) under ice-cooling, and the mixture was stirred for 1.5 hours at ambient temperature. Insoluble material was filtered off, and the filtrate was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=3:1, v/v) to give 2-amino-3-methoxy-N-methylaniline (687 mg).

Workup

  1. additionwas added
  2. temperaturecooling
  3. filtrationInsoluble material was filtered off
  4. washthe filtrate was washed with water and brine
  5. dry with materialdried over magnesium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by silica gel column chromatography (hexane

Sources & evidence

ORD record
ord-50eb49c46bcb4e199c7c3d10d594fb4f
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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