HCID 13290537, compound → HCID 15589117, compound

HRID 1262456Notes

Reaction equation

HRID 1262456 reaction equation
[N:1]([O-])=O.[Na+].[NH2:5][C:6]1[CH:11]=[C:10]([C:12]([F:15])([F:14])[F:13])[CH:9]=[CH:8][C:7]=1[NH:16][C:17]1[CH:30]=[CH:29][C:20]([O:21][CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][CH:18]=1>O.Cl>[F:13][C:12]([F:15])([F:14])[C:10]1[CH:9]=[CH:8][C:7]2[N:16]([C:17]3[CH:18]=[CH:19][C:20]([O:21][CH:22]([CH3:28])[C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:29][CH:30]=3)[N:1]=[N:5][C:6]=2[CH:11]=1

Participants

5

Reactant 2

HCID 13290537HCID 13290537, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 15589117HCID 15589117, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Procedure

A solution of 2.1 g of sodium nitrite in 25 ml of water was added drop-by-drop over a 5-minute period to a stirred solution of 7.4 g of 1C in 150 ml of 12% hydrochloric acid, at 0° C. The mixture then was allowed to warm to room temperature and was stirred for 24 hours. It then was diluted with 200 ml of water and extracted with ether. The ether extract was dried (MgSO4), filtered and concentrated to dryness. The residue was absorbed on silica gel and chromatographed, using as eluent a 2:15:33 v/v/v mixture of tetrahydrofuran, ethyl acetate and hexane (hereinafter, Solvent A), to give 1, as an amber syrup.

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. dry with materialwas dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated to dryness
  6. customThe residue was absorbed on silica gel
  7. customchromatographed
  8. additiona 2:15:33 v/v/v mixture of tetrahydrofuran, ethyl acetate and hexane (hereinafter, Solvent A),
  9. customto give 1

Sources & evidence

ORD record
ord-b336ee7c85dd424b8f9395c6901be1d4
Source dataset
uspto-grants-1984_06
Patent number
US04452626

Reaction notes

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