3-benzyloxy-2-nitro-N-methylaniline → 3-benzyloxy-N1-methylbenzene-1,2-diamine hydrochloride

HRID 1430419Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1430419
[CH2:1]([O:8][C:9]1[C:10]([N+:17]([O-])=O)=[C:11]([CH:14]=[CH:15][CH:16]=1)[NH:12][CH3:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[ClH:23]>[C].[Pt].C1(C)C=CC=CC=1>[ClH:23].[CH2:1]([O:8][C:9]1[CH:16]=[CH:15][CH:14]=[C:11]([NH:12][CH3:13])[C:10]=1[NH2:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 2

HCID 107298903-benzyloxy-2-nitro-N-methylanilineHCID 21887872Ethanol hydrochloride

Produkt 1

HCID 679540383-benzyloxy-N1-methylbenzene-1,2-diamine hydrochlorideAusbeute 85 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178503042HCID 178503042, VerbindungKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

0.80 g of 5% platinum carbon (dry) was added to a toluene (80 mL) suspension of 3-benzyloxy-N-methyl-2-nitroaniline (7.19 g, 27.8 mmol), and catalytic hydrogenation reaction was performed under ordinary pressure. The reaction solution was filtered to remove a catalyst, and the catalyst was washed with toluene (10 mL). The washing liquid was added to the precedent filtrate. A 1N hydrochloric acid ethanol solution (28 mL, 28.0 mmol) was added to the mixture under ice cooling, and the mixture was stirred under the same temperature for 30 minutes. The solvent was distilled off under reduced pressure at 20° C. or less. Precipitated crystals were collected by filtration, washed with toluene (15 mL), and dried at 40° C., thereby obtaining 6.30 g of an orange, crystal target compound (yield: 85%).

Aufarbeitung

  1. filtrationThe reaction solution was filtered
  2. customto remove a catalyst
  3. washthe catalyst was washed with toluene (10 mL)
  4. additionThe washing liquid was added to the precedent filtrate
  5. distillationThe solvent was distilled off under reduced pressure at 20° C. or less
  6. customPrecipitated crystals
  7. filtrationwere collected by filtration
  8. washwashed with toluene (15 mL)
  9. customdried at 40° C.

Quellen und Nachweise

ORD-Eintrag
ord-9dd3c065221c40f79cec656a75dee029
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940889B2

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