Sodium Hydroxide → 7-iodo-8-methoxy-5-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

HRID 221240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 221240
FC(F)(F)C([N:5]1[CH2:11][CH:10]([CH3:12])[C:9]2[CH:13]=[C:14]([I:19])[C:15]([O:17][CH3:18])=[CH:16][C:8]=2[CH2:7][CH2:6]1)=O.[OH-].[Na+]>CO.O>[I:19][C:14]1[C:15]([O:17][CH3:18])=[CH:16][C:8]2[CH2:7][CH2:6][NH:5][CH2:11][CH:10]([CH3:12])[C:9]=2[CH:13]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 22292785N-trifluoroacetyl-8-iodo-7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine

Produkt 1

HCID 100643867-iodo-8-methoxy-5-methyl-2,3,4,5-tetrahydro-1H-3-benzazepineAusbeute 92,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A solution of N-trifluoroacetyl-8-iodo7-methoxy-1-methyl-2,3,4,5-tetrahydro-1H-3-benzazepine (0.600 g, 1.45 mmol) in methanol (20 mL) was treated with 15% aqueous NaOH (20 mL), and stirred for 3 hours at 50 C. The product mixture was diluted with water (100 mL), extracted twice with EtOAc (100 mL), the combined organic phases were washed with brine (100 mL), dried with Na2SO4 and concentrated to give 0.425 g of a yellow solid. 1H NMR (400 MHz, CDCl3) d 7.52 (s, 1 H), 6.57 (s, 1H), 3.86 (s, 3 H), 3.12-3.06 (m, 4 H), 2.95 (m, 2 H), 2.75 (m, 1 H), 2.43 (bs, 1 H), 1.33 (d, J=8 Hz, 3 H). MS calculated for C12H16INO+H: 318, observed: 318.

Aufarbeitung

  1. extractionextracted twice with EtOAc (100 mL)
  2. washthe combined organic phases were washed with brine (100 mL)
  3. dry with materialdried with Na2SO4
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-2ea3760e4bcf418cbcb2cbd472d12d41
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08207158B2

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