1-Bromopentane → HCID 19363434, compound

HRID 850451Notes

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH3:12])[C:5]([OH:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].[CH2:19](Br)[CH2:20][CH2:21][CH2:22][CH3:23]>CN(C=O)C>[CH3:12][O:11][C:10]1[CH:9]=[CH:8][C:4]([C:5]([O:7][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])=[O:6])=[CH:3][C:2]=1[NH:1][CH2:9][CH2:10][CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 100 °C

Procedure

3-Amino-4-methoxybenzoic acid (1.53 g, 6.45 mmol), DMF (15 ml), potassium carbonate (2.07 g, 15 mmol) and pentyl bromide (1.86 ml, 15 mmol) were mixed, and the solution was stirred at 100° C. for 10.5 hours. The reaction mixture was filtered to remove the inorganic salt, and DMF was evaporated under reduced pressure. The obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate=10/1) to give pentyl 4-methoxy-3-pentylaminobenzoate (1.32 g, 67%) and pentyl 3-dimethylamino-4-methoybenzoate (334 mg, 14%) as colorless oils. pentyl 4-methoxy-3-pentylaminobenzoate

Workup

filtrationThe reaction mixture was filtered
customto remove the inorganic salt, and DMF
customwas evaporated under reduced pressure
customThe obtained residue was purified by column chromatography on silica gel (hexane/ethyl acetate=10/1)

Sources & evidence

ORD record: ord-8cfde05634bb48209d2b6715856ba206
Source dataset: uspto-grants-2000_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06017919

Reaction notes

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