Ammonia → HCID 178524298, compound

HRID 1023840Notes

Reaction equation

HRID 1023840 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:26]=[CH:25][CH:24]=[CH:23][C:7]=2[O:8][CH2:9][C:10]([C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=2[C:14]([O:16]CC)=[O:15])=[O:11])[N:3]=[CH:2]1.[Li+].[OH-].Cl.N>O1CCCC1.O>[NH:1]1[CH:5]=[C:4]([C:6]2[CH:26]=[CH:25][CH:24]=[CH:23][C:7]=2[O:8][CH2:9][C:10]([C:12]2[CH:22]=[CH:21][CH:20]=[CH:19][C:13]=2[C:14]([OH:16])=[O:15])=[O:11])[N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178468797HCID 178468797, compound

Product 1

HCID 178524298HCID 178524298, compoundYield 46%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(2-(2-(1H-imidazol-4-yl)phenoxy)acetyl)benzoate (0.142 mmol) in a mixture of tetrahydrofuran (2 mL) and water (1 mL) was added LiOH.H20 (0.713 mmol). After stirring for 5 h the reaction mixture was acidified with 6N HCl and treated with NH3 (solution in ethanol) till the pH was basic, the solution was concentrated under reduced pressure and subjected to column chromatography to afford the final product. Yield 46%. (CDCl3+CD3OD): 4.69 (s, 2H), 6.87 (d, 1H, J=6.18 Hz), 6.95 (t, 1H, J=5.55 Hz), 7.19 (t, 1H, J=5.79 Hz), 7.38 (d, 1H, J=5.10 Hz), 7.47-7.56 (m, 4H), 7.79 (d, 1H, J=5.00 Hz), 8.21 (br s, 1H).

Workup

  1. concentrationthe solution was concentrated under reduced pressure

Sources & evidence

ORD record
ord-fcd25880ba9540caa753762a97ebfcf7
Source dataset
uspto-grants-2014_05
Patent number
US08722720B2

Reaction notes

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