6-Methoxy-2,2-dimethyl-3-(3-nitrobenzylidene)chroman-4-one → 3-(3-Aminobenzyl)-6-methoxy-2,2-dimethylchroman-4-one

HRID 1684627Notes

Reaction equation

HRID 1684627 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[C:7](=[CH:15][C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-])=O)[CH:17]=1)[C:6]2=[O:25].[H][H]>[Pd].C(OCC)(=O)C.O1CCCC1>[NH2:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][CH:7]1[C:6](=[O:25])[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([O:2][CH3:1])[CH:4]=2)[O:9][C:8]1([CH3:13])[CH3:14]

Participants

6

Reactant 2

HCID 544784566-Methoxy-2,2-dimethyl-3-(3-nitrobenzylidene)chroman-4-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 190399713-(3-Aminobenzyl)-6-methoxy-2,2-dimethylchroman-4-oneYield 99%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A mixture of 7.3 g (0.0125) of the product of Example 110 and 700 mg 5% palladium on carbon in 200 mL ethyl acetate and 50 mL tetrahydrofuran was shaken in a Parr hydrogenator under 30 psi hydrogen for 3 hours. The mixture was filtered through Celite and concentrated to give an oil. Flash chromatography on silica gel eluting with 50% ethyl acetate in hexanes yielded 6.8 g (99%) of the title product as an oil. NMR (CDCl3): δ1.38 (s, 3H); 1.47 (s, 3H); 2.20 (dd, 1H); 2.90 (m, 1H); 3.00 (dd, 1H); 3.60 (s, br, 2H); 3.78 (s, 3H). MS (Cl, NH3) m/e: 329 (M+ +18), 312 (M+ +1,2 100).

Workup

  1. filtrationThe mixture was filtered through Celite
  2. concentrationconcentrated
  3. customto give an oil

Sources & evidence

ORD record
ord-e7068cc2a0a14842acf8159a1897821d
Source dataset
uspto-grants-1997_06
Patent number
US05641789

Reaction notes

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