Hydrazine hydrate (1:1) → 2-(4-Oxo-3,4-dihydro-phthalazin-1-ylmethyl)-isonicotinonitrile

HRID 1445710Notes

Reaction equation

[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[CH:11][C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][N:19]=2)[C:15]#[N:16])O1.O.[NH2:21][NH2:22]>O>[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([CH2:11][C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][N:19]=2)[C:15]#[N:16])=[N:22][NH:21]1

Participants

Conditions

Temperature: 90 °C

Procedure

To crude 2-(3-oxo-3H-isobenzofuran-1-ylidenemethyl)-isonicotinonitrile (iii-int)(approx 4.0 mmol) suspended in water (30 mL) and hydrazine monohydrate (2 mL). The reaction mixture was then heated to 90° C. for 90 minutes and then cooled to room temperature. The resulting suspension was filtered and washed with methanol (5 mL), water (10 ml) and then ethyl ether (2×30 mL). A buff solid was isolated with single peak in LC-MS analysis. (0.61 g, 26.7% over 3 steps); m/z (LC-MS, ESP), RT=3.48 mins, (M+H)=263.0.

Workup

temperaturecooled to room temperature
filtrationThe resulting suspension was filtered
washwashed with methanol (5 mL), water (10 ml)
customA buff solid was isolated with single peak in LC-MS analysis

Sources & evidence

ORD record: ord-707c03f7e70c49719489a2c017879dfa
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07666870B2

Reaction notes

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