Triethylamine → 6-Methoxy-1,2,3,4-tetrahydronaphthalene-2-carboxamide

HRID 654236Notes

Reaction equation

C([N:3](CC)CC)C.ClC(OCC)=O.[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH2:22][CH:21]([C:26]([OH:28])=O)[CH2:20][CH2:19]2.[NH4+].[OH-]>CC(C)=O>[CH3:14][O:15][C:16]1[CH:17]=[C:18]2[C:23](=[CH:24][CH:25]=1)[CH2:22][CH:21]([C:26]([NH2:3])=[O:28])[CH2:20][CH2:19]2

Participants

Conditions

Temperature: -10 °C

Procedure

A solution of triethylamine (2.7 ml, 0.019 mol) and ethyl chloroformate (2 ml, 0.021 mol) in acetone (40 ml) is added to a solution of the acid obtained in step (i) (3 g, 0.014 mol) in acetone (50 ml) cooled to -10° C. After 1,5 hours at -10° C., concentrated NH4OH (4.5 ml, 0.036 mol) is added dropwise and the reaction mixture is allowed to stand at -10° C. for 1 hour and at room temperature overnight. The solution is concentrated under vacuum, ethyl acetate (150 ml) is added to the obtained residue and the solution is washed sequentially with water, a saturated sodium bicarbonate solution, 6N hydrochloric acid, and water, then it is dried and concentrated to dryness. The residue is triturated with isopropyl ether and filtered thus affording 1.7 g of the above indicated amide; m.p. 136°-138° C.; [α]=+40.2° (c= 1.4%, CHCl3).

Workup

waitAfter 1,5 hours at -10° C.
concentrationThe solution is concentrated under vacuum, ethyl acetate (150 ml)
additionis added to the obtained residue
washthe solution is washed sequentially with water
dry with materiala saturated sodium bicarbonate solution, 6N hydrochloric acid, and water, then it is dried
concentrationconcentrated to dryness
customThe residue is triturated with isopropyl ether
filtrationfiltered thus

Sources & evidence

ORD record: ord-fc13c33b733949479443c67588df05c4
Source dataset: uspto-grants-1992_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05130339

Reaction notes

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