Chlorosuccinimide → 6-Amino-5-chloro-7-cyanoindan-1-ol

HRID 1947775Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1947775
[NH2:1][C:2]1[C:10]([C:11]#[N:12])=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:13])=[CH:4][CH:3]=1.[Cl:14]N1C(=O)CCC1=O.[BH4-].[Na+]>O1CCCC1>[NH2:1][C:2]1[C:10]([C:11]#[N:12])=[C:9]2[C:5]([CH2:6][CH2:7][CH:8]2[OH:13])=[CH:4][C:3]=1[Cl:14]

Komponenten

5

Edukt 3

HCID 31398ChlorosuccinimideHCID 4311764Sodium borohydrideHCID 59549438HCID 59549438, Verbindung

Produkt 1

HCID 684986706-Amino-5-chloro-7-cyanoindan-1-olAusbeute 47,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 6-amino-7-cyanoindan-1-ol (700 mg, 4 mmol) in tetrahydrofuran (50 ml) is treated with N-chlorosuccinimide (530 mg, 4 mmol) in portions over 20 minutes, stirred for 30 minutes, treated with sodiumborohydride (270 mg), and stirred for one hour. The mixture is quenched with water (30 ml), evaporated to remove tetrahydrofuran, and extracted with ethyl acetate. The organic layer is dried over sodium sulfate, filtered, and evaporated to give 6-amino-5-chloro-7-cyanoindan-1-ol (400 mg) which is directly used in the next step; LC/MS: 209/211 (M+1)+.

Aufarbeitung

  1. stirringstirred for one hour
  2. customThe mixture is quenched with water (30 ml)
  3. customevaporated
  4. customto remove tetrahydrofuran
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer is dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-67bd9fa8040e49df99a26dd4a0e4422a
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399490B2

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