Acetic Acid → Methyl 4-(7-carbamoylnaphth-1-ylmethyl)-3-methoxybenzoate

HRID 2371813Notes

Reaction equation

[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=2[O:24][CH3:25])=[CH:5][CH:4]=1)#[N:2].C(O)(=[O:28])C.B(F)(F)F.[OH-].[Na+]>C(Cl)Cl>[C:1]([C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[CH:8][CH:9]=[C:10]2[CH2:13][C:14]2[CH:23]=[CH:22][C:17]([C:18]([O:20][CH3:21])=[O:19])=[CH:16][C:15]=2[O:24][CH3:25])=[CH:5][CH:4]=1)(=[O:28])[NH2:2]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of methyl 4-(7-cyanonaphth-1-ylmethyl)-3-methoxybenzoate (394 mg), acetic acid (0.68 ml) and BF3 -etherate (0.22 ml) was heated to 120° C. for 15 min. After cooling, to the reaction mixture was added methylene chloride (50 ml) and 6N sodium hydroxide (3.5 ml) and it was stirred for 10 min. The aqueous layer was extracted with methylene chloride. The combined organic extract was washed (brine) and dried (MgSO4). Evaporation and trituration with hot ethyl acetate afforded methyl 4-(7-carbamoylnaphth-1-ylmethyl)-3-methoxybenzoate (262 mg, 63%) as a white solid; mp 215.0°-216.5° C.; MS(CI), m/e=350(M+H).

Workup

temperatureAfter cooling, to the reaction mixture
extractionThe aqueous layer was extracted with methylene chloride
extractionThe combined organic extract
washwas washed (brine)
dry with materialdried (MgSO4)
customEvaporation and trituration with hot ethyl acetate

Sources & evidence

ORD record: ord-fb27b8402dce40adaa4c2c87f86cf071
Source dataset: uspto-grants-1992_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05095038

Reaction notes

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