Hydrochloric Acid → HCID 2907754, compound

HRID 842770Notes

Reaction equation

HRID 842770 reaction equation
C1O[C:4]2([CH2:9][CH2:8][N:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N+:16]([O-:18])=[O:17])[CH2:6][CH2:5]2)[O:3]C1.Cl>CCOCC>[N+:16]([C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=1[N:7]1[CH2:8][CH2:9][C:4](=[O:3])[CH2:5][CH2:6]1)([O-:18])=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 22220290HCID 22220290, compound

Product 1

HCID 2907754HCID 2907754, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 7 (7.44 g, 28.1 mmol) in ether (300 mL) was treated with 5% aqueous HCl (150 mL). The mixture was stirred at room temperature (5 d). The reaction was quenched with solid sodium bicarbonate. The aqueous layer was extracted with three additional portions of ether and the combined organic extracts were washed with brine, dried over Na2SO4, and concentrated under reduced pressure. Flash chromatography on silica gel (20% ethyl acetate/hexane) afforded the title compound (8).

Workup

  1. customThe reaction was quenched with solid sodium bicarbonate
  2. extractionThe aqueous layer was extracted with three additional portions of ether
  3. washthe combined organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-88dd68d431cd42739171bad06f610338
Source dataset
uspto-grants-2002_04
Patent number
US06376503B1

Reaction notes

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