Ammonia → 7-Amino-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

HRID 14475Notes

Reaction equation

HRID 14475 reaction equation
C(=[N:14][C:15]1[CH:24]=[C:23]2[C:18]([C:19](=[O:35])[C:20]([C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)=[C:21]([CH:25]([CH3:27])[CH3:26])[O:22]2)=[CH:17][CH:16]=1)(C1C=CC=CC=1)C1C=CC=CC=1.Cl.N>O1CCCC1>[NH2:14][C:15]1[CH:24]=[C:23]2[C:18]([C:19](=[O:35])[C:20]([C:28]3[CH:29]=[CH:30][C:31]([Cl:34])=[CH:32][CH:33]=3)=[C:21]([CH:25]([CH3:26])[CH3:27])[O:22]2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 866256137-(Benzhydrylideneamino)-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

Product 1

HCID 116811907-Amino-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-(benzhydrylideneamino)-3-(4-chlorophenyl)-2-isopropyl-chromen-4-one (5.72 g, 12 mmol) in tetrahydrofuran (150 ml) is treated with 2M HCl solution (150 ml) and allowed to stir at room temperature for 1 hour. The solution is basified with 17% ammonia solution (150 ml), and the mixture is extracted with ethyl acetate (3×200 ml). The organic extracts are combined, dried (MgSO4), filtered and concentrated to afford a yellow suspension. The suspension is triturated with hexanes to afford the title compound as a pale yellow solid, which is isolated by filtration and dried in vacuo overnight.

Workup

  1. extractionthe mixture is extracted with ethyl acetate (3×200 ml)
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto afford a yellow suspension
  6. customThe suspension is triturated with hexanes

Sources & evidence

ORD record
ord-eb3fa833e9984931ac0a2ad081535a12
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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