2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 12361097, compound

HRID 1768868Notes

Reaction equation

HRID 1768868 reaction equation
N1C2C(=CC=CC=2)C(C2[O:14]C(C)N(C(OC)=O)C=2)=C1.[C:20]([NH:23][CH:24]([CH2:29][C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[NH:32][CH:31]=1)[C:25]([O:27][CH3:28])=[O:26])(=[O:22])[CH3:21].C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N>O1CCCC1>[C:20]([NH:23][CH:24]([C:29]([C:30]1[C:38]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[NH:32][CH:31]=1)=[O:14])[C:25]([O:27][CH3:28])=[O:26])(=[O:22])[CH3:21]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 582449HCID 582449, compoundHCID 18949367HCID 18949367, compound

Product 1

HCID 12361097HCID 12361097, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Oikawa et al. (J. Org. Chem., vol. 42, pp. 1213-1216, 1977) describes preparation of methyl 5-(3-indolyl)-2-methyloxazole-3-carboxylate in 33% yield by oxidation of methyl 2-acetamido-3-(3-indolyl)propionate with DDQ in tetrahydrofuran. Use of aqueous tetrahydrofuran gave methyl 2-acetamido-3-(3-indolyl)-3-oxopropionate in 84% yield. Preparation of the corresponding thiazole or imidazole is not described.

Sources & evidence

ORD record
ord-4950d19b2e844551beb1587c71797ce3
Source dataset
uspto-grants-1995_01
Patent number
US05378803

Reaction notes

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