Thionyl Chloride → 1,2,3,4-Tetrahydrophthalazine

HRID 2415687Notes

Reaction equation

HRID 2415687 reaction equation
C(OC([N:8]1[N:17](C(OC(C)(C)C)=O)[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH2:9]1)=O)(C)(C)C.O=S(Cl)Cl>CO>[CH2:9]1[C:10]2[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH2:16][NH:17][NH:8]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15322838HCID 15322838, compound

Product 1

HCID 831841,2,3,4-Tetrahydrophthalazine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1,4-dihydrophthalazine-2,3-dicarboxylic acid di-tert-butyl ester, 4, (1.0 g, 3 mmol) is dissolved in MeOH (20 mL) and SOCl2 (0.5 mL) added dropwise. After stirring at room temp for 72 hours, the solvent is removed in vacuo to afford 0.6 g of the desired product as white solid.

Workup

  1. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-cbb1ab4d149548338813ca03df9f117c
Source dataset
uspto-grants-2004_11
Patent number
US06821971B2

Reaction notes

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