5-Oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid → HCID 16048458, compound

HRID 1690679Notes

Reaction equation

O=[C:2]1[CH2:11][CH2:10][CH2:9][C:8]2[CH:7]=[C:6]([C:12]([OH:14])=[O:13])[CH:5]=[CH:4][C:3]1=2.Cl.[CH2:16]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([NH:32]N)[CH:27]=2)=[CH:22][CH:21]=1)[CH2:17][CH2:18][CH3:19]>[Cl-].[Zn+2].[Cl-].C(O)(=O)C>[CH2:16]([C:20]1[CH:25]=[CH:24][C:23]([C:26]2[CH:27]=[C:28]3[C:29]([C:11]4[CH2:10][CH2:9][C:8]5[CH:7]=[C:6]([C:12]([OH:14])=[O:13])[CH:5]=[CH:4][C:3]=5[C:2]=4[NH:32]3)=[CH:30][CH:31]=2)=[CH:22][CH:21]=1)[CH2:17][CH2:18][CH3:19]

Participants

Conditions

Temperature: 105 °C

Procedure

A sample of commercially available 5-Oxo-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid (75 mg, 0.39 mmol) and (4′-Butyl-biphenyl-3-yl)-hydrazine hydrochloride (115 mg, 0.41 mmol) are treated with zinc chloride (134 mg, 0.99 mmol) and acetic acid (5 mL). The reaction is then heated to 105° C. overnight and cooled to room temperature. The reaction is filtered and the filtrate is washed with methanol and dried on the high vacuum line to afford the title material as a single regioisomer. 1H NMR (400 MHz, DMSO-d6) δ 11.63 (s, 1H), 7.90-7.84 (m, 2H), 7.75-7.71 (m, 1H), 7.62-7.57 (m, 4H), 7.35-7.31 (m, 1H), 7.28 (d, J=8.0 Hz, 2H), 3.11-3.05 (m, 2H), 2.99-2.92 (m, 2H), 2.62 (dd, J=7.6, 7.6 Hz, 2H), 1.65-1.55 (m, 2H), 1.40-1.29 (m, 2H), 0.92 (dd, J=7.3, 7.3 Hz, 3H); ESIMS m/z for (M++H+) calculated 396.2, found 396.2.

Workup

temperaturecooled to room temperature
filtrationThe reaction is filtered
washthe filtrate is washed with methanol
customdried on the high vacuum line

Sources & evidence

ORD record: ord-90d3721467ae482b8fc1b814ae6afe12
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08153671B2

Reaction notes

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