Sulfuric Acid → HCID 22467505, compound

HRID 1934658Notes

Reaction equation

[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5].[C:16]1(=O)[CH2:20][CH2:19][CH2:18][CH2:17]1.[BH4-].[Na+].S(=O)(=O)(O)O.C(=O)(O)[O-].[Na+]>O1CCCC1>[CH:16]1([NH:1][C:2]2[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:3]=2[C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:20][CH2:19][CH2:18][CH2:17]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of ethyl 2-amino-5-nitrobenzoate (5.00 g), cyclopentanone (9.00 g) and sodium borohydride (4.05 g) in anhydrous tetrahydrofuran (100 mL) was added sulfuric acid (6 mL) under ice-water cooling. The mixture was stirred for 9 hours at 0° C. and then for 15 hours at ambient temperature. The mixture was neutralized with an aqueous saturated sodium bicarbonate solution and extracted with ethyl acetate. The extract was washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by a silica gel column chromatography eluting with a mixture of hexane and ethyl acetate (5:1). The obtained product was triturated with hexane to give ethyl 2-cyclopentylamino-5-nitrobenzoate as yellow powders (5.94 g).

Workup

waitfor 15 hours at ambient temperature
extractionextracted with ethyl acetate
washThe extract was washed with water and brine
dry with materialdried over magnesium sulfate
customevaporated in vacuo
customThe residue was purified by a silica gel column chromatography
washeluting with a mixture of hexane and ethyl acetate (5:1)
customThe obtained product was triturated with hexane

Sources & evidence

ORD record: ord-37719e0369ef4c758b2d97b0671f6abe
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06384080B1

Reaction notes

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