Ethanol → HCID 178518942, compound

HRID 1667394Notes

Reaction equation

[NH2:1][NH2:2].[CH2:3]([OH:5])[CH3:4].[CH:6]([OH:9])([CH3:8])C.CN1[CH2:15][CH2:14][CH2:13][C:12]1=O>>[OH:5][C:3]1[C:4]2[C:8](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:6]([OH:9])=[N:2][N:1]=1

Participants

Reactant 4

HCID 702Ethanol

HCID 3776Isopropanol

HCID 9321Hydrazine

HCID 13387N-methyl-2-pyrrolidone

Product 1

HCID 178518942HCID 178518942, compound

Procedure

For example, as outlined in Scheme 1,1,2,4-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-5a58f344c7ad465ab4b2e53aaffcfbe4
Source dataset: uspto-grants-2011_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08044041B2

Reaction notes

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