Hydrazine → 4-Methyl-3-(7-oxo-6,7-dihydrothieno[2,3-d]pyridazin-2-yl)benzoic acid

HRID 19581Notes

Reaction equation

C([NH:5][C:6]([C:8]1[S:12][C:11]([C:13]2[CH:14]=[C:15]([CH:19]=[CH:20][C:21]=2[CH3:22])[C:16]([OH:18])=[O:17])=[CH:10][C:9]=1[CH:23]=O)=[O:7])(C)(C)C.[NH2:25]N>C(O)(=O)C>[CH3:22][C:21]1[CH:20]=[CH:19][C:15]([C:16]([OH:18])=[O:17])=[CH:14][C:13]=1[C:11]1[S:12][C:8]2[C:6](=[O:7])[NH:5][N:25]=[CH:23][C:9]=2[CH:10]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A solution of 3-(5-(tert-butylcarbamoyl)-4-formylthiophen-2-yl)-4-methylbenzoic acid (2.30 g, 6.7 mmol) in acetic acid (20 ml) was treated with hydrazine (0.73 ml, 20 mmol) and heated to 110° C. for 8 hrs. After cooling to RT the volatiles were removed in vacuo. The residue was recrystallized from MeOH. Yield: 1.01 g. MS (ESI, pos. ion) m/z: 287 (M+1).

Workup

temperatureAfter cooling to RT the volatiles
customwere removed in vacuo
customThe residue was recrystallized from MeOH

Sources & evidence

ORD record: ord-f8a2bb2e141742789ed2a7ce7dbe635c
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07745449B2

Reaction notes

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