Methyl 4-chloro-3-nitrobenzoate → Methyl 3-Amino-4-chlorobenzoate

HRID 337167

Reaktionsgleichung

Reaktionsgleichung von HRID 337167
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-])=O>C(O)(=O)C.C(=O)(O)[O-].[Na+].[Fe]>[NH2:12][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][C:2]=1[Cl:1])[C:6]([O:8][CH3:9])=[O:7]

Komponenten

5

Edukt 1

HCID 735797Methyl 4-chloro-3-nitrobenzoate

Produkt 1

HCID 593055Methyl 3-Amino-4-chlorobenzoateAusbeute 97,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 176Acetic AcidLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

A solution of methyl 4-chloro-3-nitrobenzoate (10 g) dissolved in acetic acid (100 mL) was treated with Iron powder (10.36 g) under nitrogen. The resulting mixture was stirred vigorously at 20° C. for 2 h. The reaction mixture was filtered through celite and the filtrate evaporated to dryness to afford crude product. The residue was diluted with aqueous sodium bicarbonate solution (200 mL), and extracted with dichloromethane (250 mL). The organic layer was separated, dried (MgSO4), filtered and evaporated to afford the sub title compound (8.41 g).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate evaporated to dryness
  3. customto afford crude product
  4. extractionextracted with dichloromethane (250 mL)
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-b843a2894edd481d91b08215ca37ec72
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889692B2

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