Nitrogen → 5-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran

HRID 2292484Notes

Reaction equation

HRID 2292484 reaction equation
[C:1]([C:5]1[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=[C:7]([N+:16]([O-])=O)[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].CCCCCC.N#N>CCO.[Pd]>[NH2:16][C:7]1[CH:6]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:10]2[O:11][CH2:12][C:13]([CH3:15])([CH3:14])[C:9]=2[CH:8]=1

Participants

6

Reactant 3

HCID 947NitrogenHCID 8058HexaneHCID 107531427-tert-Butyl-2,3-dihydro-3,3-dimethyl-5-nitro-benzofuran

Product 1

HCID 106804065-Amino-7-tert-butyl-2,3-dihydro-3,3-dimethylbenzofuran

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 7-tert-butyl-3,3-dimethyl-5-nitro-2,3-dihydrobenzo[b]furan (2.2 g, 8.8 mmol) and 10% Pd on charcoal (220 mg) in EtOH (60 mL) is hydrogenated at 24° C. and 40 psi of H2 for 3 h. The reaction is monitored by TLC (EtOAC:hexane, 1:19). The reaction mixture is vented to N2, filtered through Celite, and evaporated to yield 5-amino-7-tert-butyl-3,3-dimethyl-2,3-dihydrobenzo[b]furan as a purple solid.

Workup

  1. customis hydrogenated at 24° C.
  2. filtrationfiltered through Celite
  3. customevaporated

Sources & evidence

ORD record
ord-2c422301fc844979a09048bb77fd6a13
Source dataset
uspto-grants-1997_11
Patent number
US05684002

Reaction notes

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