Sodium Hydroxide → 1-(3-Methylanilino)phthalazine-4-carbaldehyde

HRID 2054183Notes

Reaction equation

[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH:16]2OCOC[O:17]2)=[N:8][N:7]=1.[OH-].[Na+]>OS(O)(=O)=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][CH:24]=1)[NH:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:9]([CH:16]=[O:17])=[N:8][N:7]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 3.15 g (9.74 mmol) 1-(3-methylanilino)-4-([1,3,5]trioxan-2-yl)phthalazine in 150 ml H2SO4 (10% in H2O) is stirred for 7 h at 100° C. The suspension is cooled to RT and adjusted to alkaline pH with NaOH (20% in H2O), the title compound that precipitates out is filtered off and washed with water, 1H-NMR (DMSO-d6) 10.17 (s, HCO), 9.84 (s, HN), 9.02 (d, 1H), 8.67 (d, 1H), 8.03 (m, 2H), 7.8-7.6 (2 sb, 2H), 7.30 (t, 1H), 6.98 (d, 1H), 2.36 (s, 3H); FAB-MS (M−H)+=262.

Workup

temperatureThe suspension is cooled to RT
customthe title compound that precipitates out
filtrationis filtered off
washwashed with water, 1H-NMR (DMSO-d6) 10.17 (s, HCO), 9.84 (s, HN), 9.02 (d, 1H), 8.67 (d, 1H), 8.03 (m, 2H), 7.8-7.6 (2 sb, 2H), 7.30 (t, 1H), 6.98 (d, 1H), 2.36 (s, 3H)

Sources & evidence

ORD record: ord-2d2a93437c2a4435bf1934021759c99d
Source dataset: uspto-grants-2008_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07329660B2

Reaction notes

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