Hydrochloric Acid → 7-Amino-3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-chromen-4-one

HRID 14510Notes

Reaction equation

HRID 14510 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13](=[O:14])[C:12]3[CH:15]=[CH:16][C:17]4[N:18]=C(C)[O:20][C:21]=4[C:11]=3[O:10][C:9]=2[CH:23]([CH3:25])[CH3:24])=[CH:4][CH:3]=1.Cl>CO>[NH2:18][C:17]1[C:21]([OH:20])=[C:11]2[C:12]([C:13](=[O:14])[C:8]([C:5]3[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=3)=[C:9]([CH:23]([CH3:24])[CH3:25])[O:10]2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 687030987-(4-Chlorophenyl)-8-isopropyl-2-methyl-chromeno[7,8-d]oxazol-6-one

Product 1

HCID 687013867-Amino-3-(4-chlorophenyl)-8-hydroxy-2-isopropyl-chromen-4-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
70 °C

Procedure

To a suspension of 7-(4-chlorophenyl)-8-isopropyl-2-methyl-chromeno[7,8-d]oxazol-6-one (650 mg, 1.84 mmol) in methanol (30 ml) is added concentrated HCl (5 ml). The reaction mixture is stirred at 70° C. for 1 h. The solvent is removed in vacuo, and the product is partitioned between CH2Cl2 and a saturated solution of NaHCO3. The organic phase is washed with water and brine, dried (MgSO4) and concentrated in vacuo to give the title compound as a pale yellow solid.

Workup

  1. customThe solvent is removed in vacuo
  2. customthe product is partitioned between CH2Cl2
  3. washThe organic phase is washed with water and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d0ce4eb92472410f843048d257b3e744
Source dataset
uspto-grants-2010_06
Patent number
US07732435B2

Reaction notes

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