Aluminium lithium hydride → 1-(4-Methoxybenzyl)-5-(methylamino)-6-oxo-1,6-dihydropyridazine-4-carbaldehyde

HRID 1966382Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:24]=[CH:23][C:6]([CH2:7][N:8]2[C:13](=[O:14])[C:12]([NH:15][CH3:16])=[C:11]([C:17](N(OC)C)=[O:18])[CH:10]=[N:9]2)=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][N:8]2[C:13](=[O:14])[C:12]([NH:15][CH3:16])=[C:11]([CH:17]=[O:18])[CH:10]=[N:9]2)=[CH:23][CH:24]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A solution of 1-(4-methoxybenzyl)-N-methoxy-N-methyl-5-(methylamino)-6-oxo-1,6-dihydropyridazine-4-carboxamide (3) (4.60 g, 13.8 mmol) in THF (50.0 mL) was treated with 1.0 M LAH in THF (15 mL, 15 mmol) at −78° C. The mixture was stirred at 0° C. for 1 h then quenched carefully at 0° C. with MeOH (1.0 mL), followed by water (1.0 mL) and 1 M aq HCl (1.0 mL). The resulting suspension was filtered and the filtrate was concentrated in vacuo to give 1-(4-methoxybenzyl)-5-(methylamino)-6-oxo-1,6-dihydropyridazine-4-carbaldehyde as a pale yellow solid. MS (ESI, pos. ion) m/z: 274 (M+1).

Workup

customthen quenched carefully at 0° C. with MeOH (1.0 mL)
filtrationThe resulting suspension was filtered
concentrationthe filtrate was concentrated in vacuo

Sources & evidence

ORD record: ord-94fdb08c9fa54c6f876b853eb677b19c
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08420649B2

Reaction notes

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