Ethanol → HCID 178518942, compound

HRID 1803480Notes

Reaction equation

HRID 1803480 reaction equation
[CH:1]1[C:6](C(O)=O)=[CH:5][C:4]2[C:10](O[C:13](=[O:14])[C:3]=2[CH:2]=1)=[O:11].[NH2:15][NH2:16].C(O)C.C(O)(C)C>CN1CCCC1=O>[OH:11][C:10]1[C:4]2[C:3](=[CH:2][CH:1]=[CH:6][CH:5]=2)[C:13]([OH:14])=[N:16][N:15]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 3776IsopropanolHCID 9321HydrazineHCID 11089Trimellitic anhydride

Product 1

HCID 178518942HCID 178518942, compound

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

For example, as outlined in Scheme I, 1,2,4-benzene tricarboxylic anhydride 1 may be reacted with hydrazine in a suitable solvent, e.g., ethanol, isopropyl alcohol, or n-methyl-2-pyrrolidinone, to produce dihydroxy-phthalazine 2. Compound 2 may then be reacted with SOCl2 and POCl3 to produce a trichloride intermediate that is reacted immediately with an amine X1X2NH (where X1 and X2 are, e.g., hydrogen, alkyl, aryl, etc.) to produce an amide compound 3. Compound 3 may then be reacted with NaI and HI in a suitable solvent, e.g., acetone, to produce a di-iodo compound 4. Compound 4 may then be further reacted with a suitable nucleophile in a suitable solvent to form a mixture of the two correspondent regioisomers 5 and 6. Replacement of any remaining iodine atoms may be achieved using standard nucleophilic substitution and/or transition metal reactions known to one of skill in the art, for example, Stille and Suzuki type reactions.

Sources & evidence

ORD record
ord-ddaedfc22d2542469c0c10f2368a12f2
Source dataset
uspto-grants-2013_01
Patent number
US08349836B2

Reaction notes

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