Sodium Hydroxide → HCID 15280227, compound

HRID 1647248Notes

Reaction equation

HRID 1647248 reaction equation
S(Cl)([Cl:3])=O.[Cl:5][C:6]1[CH:21]=[CH:20][C:9]2[CH:10](O)[C:11]3[C:16]([CH2:17][O:18][C:8]=2[CH:7]=1)=[CH:15][CH:14]=[CH:13][N:12]=3.[OH-].[Na+]>ClCCl>[Cl:5][C:6]1[CH:21]=[CH:20][C:9]2[CH:10]([Cl:3])[C:11]3[C:16]([CH2:17][O:18][C:8]=2[CH:7]=1)=[CH:15][CH:14]=[CH:13][N:12]=3

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 15280226HCID 15280226, compound

Product 1

HCID 15280227HCID 15280227, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

Add thionyl chloride (2.74 mL, 4.48 g, 37.6 mmole) to 8-chloro-5,11-dihydro[1]benzoxepino[4,3-b]pyridin-11-ol (8.48 g, 34.2 mmole) in dichloromethane (100 mL) at 0° C. under a nitrogen atmosphere. Stir for 30 minutes at 0° C., and then stir for 60 minutes at room temperature. Add iced 1.5N NaOH (100 mL), and separate layers. Extract aqueous solution with dichloromethane (2×100 mL). Wash the combined organic solution with water and saturated NaCl, dry with MgSO4, filter, and concentrate in vacuo to give a reddish-black oil (8.82 g, 97% yield).

Workup

  1. stirringstir for 60 minutes at room temperature
  2. customseparate layers
  3. washWash the combined organic solution with water and saturated NaCl
  4. dry with materialdry with MgSO4
  5. filtrationfilter
  6. concentrationconcentrate in vacuo

Sources & evidence

ORD record
ord-b0f597251eae4bd08e5a639fcd2daaee
Source dataset
uspto-grants-1995_07
Patent number
US05430032

Reaction notes

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