Hydrochloric Acid → 2-butylbenzofuran-5-amine Hydrochloride

HRID 971080Notes

Reaction equation

HRID 971080 reaction equation
[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([NH:14]C(=O)C)=[CH:10][C:8]=2[CH:9]=1)[CH2:2][CH2:3][CH3:4].[ClH:18]>>[ClH:18].[CH2:1]([C:5]1[O:6][C:7]2[CH:13]=[CH:12][C:11]([NH2:14])=[CH:10][C:8]=2[CH:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 9899437N-(2-Butyl-1-benzofuran-5-yl)acetamide

Product 1

HCID 98133102-butylbenzofuran-5-amine HydrochlorideYield 88.6%

Conditions

Temperature
2.5 °C

Procedure

A mixture of N-(2-butyl-5-benzofuranyl)acetamide [10a] (1.16 g, 5.0 mmol) and 15% hydrochloric acid (10 mL) was stirred overnight under reflux conditions and 2 hours at 0-5° C. The precipitated crystals were filtered off, washed on the filter with cold water and ethyl acetate and dried under reduced pressure at 50° C. (water bath) to a constant weight to give 1.00 g (88.6%) of 2-butyl-5-benzofuranamine hydrochloride [12a] as off-white crystalls with mp 189-192° C. (with decomposition).

Workup

  1. filtrationThe precipitated crystals were filtered off
  2. washwashed on the
  3. filtrationfilter with cold water and ethyl acetate
  4. dry with materialdried under reduced pressure at 50° C. (water bath) to a constant weight

Sources & evidence

ORD record
ord-31e5a78a2f284e2bbd05a34bddd7aafa
Source dataset
uspto-grants-2007_12
Patent number
US07312345B2

Reaction notes

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