Hydrochloric Acid → 5-Amino-7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine

HRID 2271081Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2271081
[Cl:1][C:2]1[CH:3]=[C:4]([CH3:14])[C:5]2[O:11][CH2:10][CH2:9][CH2:8][C:7](=O)[C:6]=2[CH:13]=1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:21].[Na+].Cl>CO>[NH2:21][CH:7]1[C:6]2[CH:13]=[C:2]([Cl:1])[CH:3]=[C:4]([CH3:14])[C:5]=2[O:11][CH2:10][CH2:9][CH2:8]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 517165Ammonium AcetateHCID 43472547-Chloro-9-methyl-3,4-dihydro-2H-benzo[b]oxepin-5-oneHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 223917895-Amino-7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepineAusbeute 61,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

3.0 g of 7-chloro-9-methyl-3,4-dihydro-2H-1-benzoxepin-5-one, 50 ml of anhydrous methanol, 10.9 g of ammonium acetate and 0.63 g of sodium cyanoborohydride were stirred for 5 h at 60° C. and then for 2 days at RT. The reaction mixture was then acidified with hydrochloric acid and then concentrated on a rotary evaporator. The residue was taken up in water, and the solution was rendered alkaline with ammonia solution and extracted with EA. After drying and concentrating, the product was purified by chromatography on silica gel using ethyl acetate/methanol 9:1 and 1.3 g of 5-amino-7-chloro-9-methyl-2,3,4,5-tetrahydro-1-benzoxepine were obtained.

Aufarbeitung

  1. concentrationconcentrated on a rotary evaporator
  2. extractionextracted with EA
  3. customAfter drying
  4. concentrationconcentrating
  5. customthe product was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-f5c39af47cb646ce8e7c41d37c4c9f3d
Quelldatensatz
uspto-grants-2001_12
Patentnummer
US06333349B1

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