Ammonia → 1,3-dihydro-7-hydroxyamino-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

HRID 1729600

Reaktionsgleichung

Reaktionsgleichung von HRID 1729600
[CH3:1][N:2]1[C:8]2[CH:9]=[CH:10][C:11]([N+:13]([O-])=[O:14])=[CH:12][C:7]=2[C:6]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[N:5][CH2:4][C:3]1=[O:22].O1CCCC1.O.O.O.C([O-])(=O)C.[Na+].N>C(Cl)Cl.CO>[OH:14][NH:13][C:11]1[CH:10]=[CH:9][C:8]2[N:2]([CH3:1])[C:3](=[O:22])[CH2:4][N:5]=[C:6]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:7]=2[CH:12]=1

Komponenten

7

Edukt 4

HCID 222AmmoniaHCID 4496NimetazepamHCID 8028TetrahydrofuranHCID 23665404Sodium Acetate Trihydrate

Produkt 1

HCID 123178981,3-dihydro-7-hydroxyamino-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 15 g. (0.05 mol) of 1,3-dihydro-1-methyl-7-nitro-5-phenyl-2H-1,4-benzodiazepin-2-one, 250 ml. of tetrahydrofuran, 250 ml. of methanol, 56 g. of stannous chloride dihydrate and 68 g. of sodium acetate trihydrate was stirred under nitrogen for 3 hours. 1 l. of methylene chloride and 15 ml. of concentrated ammonia was added. The inorganic material was separated by filtration over celite. The filtrate was washed with 1N sodium hydroxide solution, was dried over sodium sulfate and evaporated. Crystallization of the residue from methylene chloride and recrystallization from ethanol/methylene chloride yielded light yellow product with m.p. 211°-213°.

Aufarbeitung

  1. additionA mixture of 15 g
  2. customThe inorganic material was separated by filtration over celite
  3. washThe filtrate was washed with 1N sodium hydroxide solution
  4. dry with materialwas dried over sodium sulfate
  5. customevaporated
  6. customCrystallization of the residue
  7. customfrom methylene chloride and recrystallization from ethanol/methylene chloride
  8. customyielded light yellow product with m.p. 211°-213°

Quellen und Nachweise

ORD-Eintrag
ord-5676a85b66054621bb6750b0242c4d8a
Quelldatensatz
uspto-grants-1976_11
Patentnummer
US03989681

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