Water → HCID 13655816, compound

HRID 2076422Notes

Reaction equation

[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](O)=[O:15])[CH:5]=[CH:4][C:3]1=2.CN(C=O)C.[NH2:23][C:24]1[CH:33]=[CH:32][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:26][CH:25]=1.O>O=S(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:12])([CH3:13])[C:8]2[CH:7]=[C:6]([C:14]([NH:23][C:24]3[CH:25]=[CH:26][C:27]([C:28]([O:30][CH3:31])=[O:29])=[CH:32][CH:33]=3)=[O:15])[CH:5]=[CH:4][C:3]1=2

Participants

Conditions

Temperature: 60 °C

Procedure

5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid 2 (0.20 g, 0.86 mmol) was dissolved in SOCl2 (4.3 mL) at 0° C. A drop of DMF was added and the mixture was stirred for 0.5 h. The SOCl2 was removed under vacuum and the crude acid chloride was dissolved in pyridine (10 mL). Methyl 4-aminobenzoate (0.143 g, 0.947 mmol) and DMAP (0.010 mg, 0.086 mmol) were added and the mixture was heated at 60° C. for 2 h with stirring. The mixture was poured into H2O and the product was extracted with EtOAc; The organic layer was washed successively with HCl (2M), saturated NaHCO3, saturated NaCl, dried over MgSO4, filtrated to give after evaporation methyl 4-(5,6,7,8-tetrahydro-5,5,8,8-tetramethylnaphthalene-2-carboxamido)benzoate 3 (0.23 g, 73% yield) as a white solid.

Workup

customThe SOCl2 was removed under vacuum
dissolutionthe crude acid chloride was dissolved in pyridine (10 mL)
stirringwith stirring
extractionthe product was extracted with EtOAc
washThe organic layer was washed successively with HCl (2M), saturated NaHCO3, saturated NaCl
dry with materialdried over MgSO4
filtrationfiltrated
customto give

Sources & evidence

ORD record: ord-c82adf03a25343eb88621a45518e8484
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923579B2

Reaction notes

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