Formaldehyde → 2-[1,1'-Biphenyl]-4-yl-3-(dimethylamino)-6-fluoro-4-quinolinecarboxylic acid

HRID 1073267Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1073267
N[C:2]1[C:3]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)=[N:4][C:5]2[C:10]([C:11]=1[C:12]([OH:14])=[O:13])=[CH:9][C:8]([F:15])=[CH:7][CH:6]=2.[CH2:28]=O.[C:30]([BH3-])#[N:31].[Na+].[BH4-].[Na+]>C(#N)C.C(O)(=O)C.O>[C:19]1([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:20]=[CH:21][C:16]([C:3]2[C:2]([N:31]([CH3:30])[CH3:28])=[C:11]([C:12]([OH:14])=[O:13])[C:10]3[C:5](=[CH:6][CH:7]=[C:8]([F:15])[CH:9]=3)[N:4]=2)=[CH:17][CH:18]=1

Komponenten

8

Edukt 4

HCID 712FormaldehydeHCID 1314193-Amino-2-(1,1'-biphenyl)-4-yl-6-fluoro-4-quinolinecarboxylic acidHCID 4311764Sodium borohydrideHCID 5003444Sodium cyanoborohydride

Produkt 1

HCID 150859562-[1,1'-Biphenyl]-4-yl-3-(dimethylamino)-6-fluoro-4-quinolinecarboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 176Acetic AcidLösungsmittel2×HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A 4 g portion of 3-amino-2-[1,1'biphenyl]-4-yl-6-fluoro-4-quinolinecarboxylic acid was dissolved in 250 ml of acetonitrile. To this was added 2.7 ml of 40% aqueous formaldehyde and the mixture was heated at 80° C. until solution was complete. A 2.1 g portion of sodium cyanoborohydride was added and the solution stirred at 20° C. for 8 hours. Glacial acetic acid was added to pH 6, then 0.69 g of sodium borohydride was added and stirring continued at 20° C. for 72 hours. The reaction mixture was poured into 1 liter of water and adjusted to pH 4 with glacial acetic acid. The solid was collected, washed with water, dried and then twice suspended in 200 ml of hot ethanol and filtered. The solid was collected, giving 2.5 g of the desired product as a yellow powder, mp 235°-239° C. (gas solution).

Aufarbeitung

  1. stirringstirring
  2. waitcontinued at 20° C. for 72 hours
  3. customThe solid was collected
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. customThe solid was collected

Quellen und Nachweise

ORD-Eintrag
ord-d3e4af4cefb54e2a9870c8d1d1e0c080
Quelldatensatz
uspto-grants-1990_11
Patentnummer
US04968702

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