Sulfuric Acid → 5-benzyloxy-N1-methylbenzene-1,2-diamine

HRID 1430409Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1430409
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([N+:17]([O-])=O)=[C:13]([CH:16]=1)[NH:14][CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(=O)(=O)(O)O>[C].[Pt].CC(O)C>[CH2:1]([O:8][C:9]1[CH:16]=[C:13]([NH:14][CH3:15])[C:12]([NH2:17])=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 1118Sulfuric AcidHCID 679540515-benzyloxy-N-methyl-2-nitroaniline

Produkt 1

HCID 679539775-benzyloxy-N1-methylbenzene-1,2-diamineAusbeute 94,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178503042HCID 178503042, VerbindungKatalysatorHCID 3776IsopropanolLösungsmittel

Versuchsvorschrift

5% platinum carbon (0.50 g, (DRY)) was added to a 2-propanol (170 mL) suspension of 5-benzyloxy-N-methyl-2-nitroaniline (10.00 g, 38.7 mmol), and catalytic hydrogenation reaction was performed at ordinary pressure. The reaction solution was filtered to remove a catalyst. The catalyst was washed with 2-propanol (20 mL), and the washing liquid was added to the precedent filtrate. Under ice cooling, 97% sulfuric acid (1.06 mL, 19.3 mmol) was added to the mixture, and then the mixture was stirred under the same temperature for 30 minutes. The resulting precipitated crystals were collected by filtration, then washed with 2-propanol (40 mL), and dried at 40° C., thereby obtaining 9.07 g of a light-purple, crystal target compound (yield: 94.7%).

Aufarbeitung

  1. filtrationThe reaction solution was filtered
  2. customto remove a catalyst
  3. washThe catalyst was washed with 2-propanol (20 mL)
  4. additionthe washing liquid was added to the precedent filtrate
  5. customThe resulting precipitated crystals
  6. filtrationwere collected by filtration
  7. washwashed with 2-propanol (40 mL)
  8. customdried at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-c1617e0b284f494d9de7aa602731dd11
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940889B2

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