Ammonium Chloride → 6-Methyl-1,3-dioxaindan-5-amine

HRID 32798

Reaction equation

HRID 32798 reaction equation
[CH3:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1.[Cl-].[NH4+]>[Fe].CO.O>[CH3:1][C:2]1[C:10]([NH2:11])=[CH:9][C:5]2[O:6][CH2:7][O:8][C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 25517Ammonium Chloride2×HCID 45504615-Methyl-6-nitro-1,3-benzodioxole

Product 1

HCID 124453406-Methyl-1,3-dioxaindan-5-amineYield 94.5%

Reagents, catalysts & solvents 2

HCID 23925IronCatalyst2×HCID 22242641Methanol--water (1/1)Solvent

Procedure

A mixture of 5-methyl-6-nitro-benzo(1,3)dioxole (50 mg, 0.28 mmol), Fe (54 mg, 3.5 eq) and ammonium chloride (51.2 mg, 3.5 eq) in a 1:1 mixture of MeOH/H2O (2.8 mL) was subjected to microwave irradiation (60W, P=100 p.s.i.) at 80° C. for four 10 min periods. The brown solution was allowed to cool to r.t. and more Fe (3.5 eq) and ammonium chloride (3.5 eq) were added. The mixture was subjected to microwave irradiation (60W, P=100 p.s.i.) at 80° C. for an additional 10 min. Fe was filtered off and the solvent evaporated. The crude product was purified on an SCX cartridge (cHex/EtOAc 9:1) to give the title compound as a brown solid (40 mg, 93%).

Workup

  1. filtrationFe was filtered off
  2. customthe solvent evaporated
  3. customThe crude product was purified on an SCX cartridge (cHex/EtOAc 9:1)

Sources & evidence

ORD record
ord-dc47ee82b9a8400b886e1229bfe8af8c
Source dataset
uspto-grants-2008_09
Patent number
US07427630B2

Linked notes

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