Hydrochloric Acid → HCID 59191351, compound

HRID 1023937Notes

Reaction equation

HRID 1023937 reaction equation
[CH2:1]([C:3]1[CH:31]=[CH:30][C:6]([O:7][C:8]2[CH:28]=[CH:27][C:11]([O:12][CH2:13][CH2:14][CH2:15][N:16]3C(=O)C4C(=CC=CC=4)C3=O)=[CH:10][C:9]=2[F:29])=[C:5]([OH:32])[CH:4]=1)[CH3:2].O.NN.Cl>CO>[NH2:16][CH2:15][CH2:14][CH2:13][O:12][C:11]1[CH:27]=[CH:28][C:8]([O:7][C:6]2[CH:30]=[CH:31][C:3]([CH2:1][CH3:2])=[CH:4][C:5]=2[OH:32])=[C:9]([F:29])[CH:10]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 24654Hydrazine hydrate (1:1)HCID 59191376HCID 59191376, compound

Product 1

HCID 59191351HCID 59191351, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-{3-[4-(4-Ethyl-2-hydroxy-phenoxy)-3-fluoro-phenoxy]-propyl}-isoindole-1,3-dione (0.096 mmol; 42 mg) in methanol (2 mL), under argon, was added hydrazine monohydrate (0.21 mmol; 10 μL). The reaction was heated to reflux for 1 h 30. After cooling to 0° C., the mixture was hydrolysed with HCl 1N and filtered. The filtrate was basified with NaOH 0.1 N (pH=11) and extracted with chloroform (3*5 ml). Combined organic phases were dried over Na2SO4, concentrated in vacuo. The title compound (13 mg; 0.04 mmol; 44%) was obtained as yellow oil, after purification by preparative TLC (dichloromethane/methanol/NH4OH: 90/10/1).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 h 30
  3. filtrationfiltered
  4. extractionextracted with chloroform (3*5 ml)
  5. dry with materialCombined organic phases were dried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2e42f25b35c4f618bb3d345fb09c249
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

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