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

HRID 2287539Notes

Reaction equation

HRID 2287539 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-99bd16870732496ebd5c6d581508c4b9
Source dataset
uspto-grants-2000_07
Patent number
US06083961

Reaction notes

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