Triethylamine → N-(4-Morpholinophenyl)-5-methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxamide

HRID 427340Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]([C:16]([OH:18])=O)[CH2:8]2.S(Cl)(Cl)=O.[O:23]1[CH2:28][CH2:27][N:26]([C:29]2[CH:35]=[CH:34][C:32]([NH2:33])=[CH:31][CH:30]=2)[CH2:25][CH2:24]1.C(N(CC)CC)C>C(Cl)Cl.O.C1(C)C=CC=CC=1>[O:23]1[CH2:24][CH2:25][N:26]([C:29]2[CH:30]=[CH:31][C:32]([NH:33][C:16]([CH:7]3[CH2:6][CH2:5][C:4]4[C:9](=[C:10]([N+:13]([O-:15])=[O:14])[CH:11]=[CH:12][C:3]=4[O:2][CH3:1])[CH2:8]3)=[O:18])=[CH:34][CH:35]=2)[CH2:27][CH2:28]1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 5-methoxy-8-nitro-1,2,3,4-tetrahydronaphthalene-2-carboxylic acid (1.3 g, 5 mmol), toluene (20 mL) and thionyl chloride (1.8 mL, 25 mmol) was heated at 80° C. for 1 h. The solvents were removed in vacuo and the residue, dissolved in methylene chloride (10 mL), was added to a solution of 4-morpholinoaniline (890 mg, 5 mmol) and triethylamine (1.0 g, 10 mmol) in methylene chloride (20 mL) at 0° C. The mixture was stirred at 20° C. for 2 h, water was added and the precipitate was filtered to yield 1.9 g (90%) of the title product as crystals: mp 251-253° C.; EIMS (70 eV) m/z (relative intensity) 411 (100, M+).

Workup

customThe solvents were removed in vacuo
dissolutionthe residue, dissolved in methylene chloride (10 mL)
filtrationthe precipitate was filtered

Sources & evidence

ORD record: ord-23a6db9b2c724219a20e1a02997779ab
Source dataset: uspto-grants-2001_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06313118B1

Reaction notes

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