HCID 18699182, compound → HCID 18007653, compound

HRID 2290162Notes

Reaction equation

HRID 2290162 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:14])([CH3:13])[O:8][C:7]2([CH3:16])[CH3:15])([O-])=O>C(O)C.C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[C:9]([CH3:14])([CH3:13])[O:8][C:7]2([CH3:16])[CH3:15]

Participants

5

Reactant 1

HCID 18699182HCID 18699182, compound2×

Product 1

HCID 18007653HCID 18007653, compoundYield 95%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 5-nitro-1,1,3,3-tetramethyl-1,3-dihydro-isobenzofuran (Compound 77, 3.8 g, 16 mmol) in 40 mL of ethanol and 10 mL of ethyl acetate was treated with 5% Pd-C (0.38 g) and the resulting reaction mixture was stirred under an atmosphere of hydrogen for 2 days. The reaction mixture was filtered over a bed of Celite™ and the filtrate was evaporated to afford the title compound (2.9 g, 95%) with trace amount of starting material. 1H NMR (300 MHz, CDCl3): δ 6.86 (d, 1H, J=8.1 Hz), 6.59 (dd, 1H J=2.0, 8.1 Hz), 7.03 (d, 1H, J=8.0 Hz), 3.73 (br s, 2H), 1.48 (s, 6H), 1.47 (s, 6H).

Workup

  1. customthe resulting reaction mixture
  2. filtrationThe reaction mixture was filtered over a bed of Celite™
  3. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-7764fdfbea85418ebcb25b7a9beef28e
Source dataset
uspto-grants-2000_07
Patent number
US06093838

Reaction notes

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