Hydrochloric Acid → 6-Tert-butylbenzo[d][1,3]dioxol-5-amine

HRID 577607Notes

Reaction equation

HRID 577607 reaction equation
[C:1]([C:5]1[C:13]([N+:14]([O-])=O)=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Cl.C(O)C>[Fe].O>[C:1]([C:5]1[C:13]([NH2:14])=[CH:12][C:8]2[O:9][CH2:10][O:11][C:7]=2[CH:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 20795028HCID 20795028, compound

Product 1

HCID 574436426-Tert-butylbenzo[d][1,3]dioxol-5-amineYield 25%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

The above prepared 5-tert-Butyl-6-nitrobenzo[d][1,3]dioxole (1.1 g, 5 mmol), Fe (5.5 g, 100 mmol) and HCl (2 ml) was added into ethanol (6 ml) and water (18 ml). The mixture was stirred for 2 h at refluxed temperature. The PH was adjusted to 7-8 and the mixture was filtered and washed with methanol. The filtrate was concentrated and purified by column chromatography (petroleum ether/ethyl acetate 1%-5%) to give 6-tert-butylbenzo[d][1,3]dioxol-5-amine (240 mg, 25%) as a red solid. LCMS: 194 [M+1]+; 1H NMR (400M): (DMSO-d6) δ 1.28 (s, 9H), 4.46 (s, 2H), 5.77 (s, 2H), 6.32 (s, 1H), 6.63 (s, 1H).

Workup

  1. temperatureat refluxed temperature
  2. filtrationthe mixture was filtered
  3. washwashed with methanol
  4. concentrationThe filtrate was concentrated
  5. custompurified by column chromatography (petroleum ether/ethyl acetate 1%-5%)

Sources & evidence

ORD record
ord-64653624358045fcb274a599d69df4cf
Source dataset
uspto-grants-2015_05
Patent number
US09040556B2

Reaction notes

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