Ammonium formate → HCID 59356083, compound

HRID 402865Notes

Reaction equation

HRID 402865 reaction equation
[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[C:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6][CH:5]=1.C([O-])=O.[NH4+]>>[Cl:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH:4]1[C:13](=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[O:6][CH2:5]1

Participants

3

Reactant 2

HCID 2723923Ammonium formateHCID 24720229HCID 24720229, compound

Product 1

HCID 59356083HCID 59356083, compoundYield 14%

Procedure

Compound 41 was prepared following the general procedure described by Wähälä and Hase, Heterocycles 1989, 28, (1), 183-186, herein incorporated by reference. To a 10 mL round bottom flask was added 2′-chloroisoflavone (152 mg, 0.592 mmol) and ammonium formate (149 mg, 2.37 mmol). The flask was purged with N2, followed by addition of methanol (8 mL) and 10% Pd/C (151 mg). The reaction was allowed to stir at room temperature and monitored by reverse phase HPLC. Upon consumption of starting material, the reaction mixture was passed through a pad of silica gel using EtOAc as the eluent. The solvent was concentrated in vacuo to afford crude 41. Purified by flash column chromatography (SiO2, 10% EtOAc/Hex) to afford 41 (21 mg, 14%) as an off-white solid. Analytical data for isoflavanone 41: 1H NMR (500 MHz, CDCl3) δ 7.98 (d, J=9.5 Hz, 1H), 7.53 (app t, J=9 Hz, 1H), 7.39-7.28 (m, 4H), 7.09-7.03 (m, 2H), 4.71-4.66 (m, 2H), 4.04-4.01 (app t, J=6.5 Hz, 1H); 13C NMR (125 MHz, CDCl3) δ 192.4, 161.8, 136.3, 133.2, 129.1, 128.9, 128.1, 128.0, 121.9, 121.3, 118.1, 71.7, 52.6; GCMS: Mass calculated for C15H11ClO2, [M]+, 259. Found 225.

Workup

  1. customCompound 41 was prepared
  2. customThe flask was purged with N2
  3. additionfollowed by addition of methanol (8 mL) and 10% Pd/C (151 mg)
  4. customUpon consumption of starting material
  5. concentrationThe solvent was concentrated in vacuo
  6. customto afford crude 41
  7. customPurified by flash column chromatography (SiO2, 10% EtOAc/Hex)

Sources & evidence

ORD record
ord-a5b4e262541647798b95d210a0deda31
Source dataset
uspto-grants-2014_06
Patent number
US08742141B2

Reaction notes

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