2,4-Dinitrobenzoic acid → HCID 22922379, compound

HRID 2258504Notes

Reaction equation

HRID 2258504 reaction equation
[N+](C1C=C([N+]([O-])=O)C=CC=1C(O)=O)([O-])=O.[N+:16]([C:19]1[CH:39]=[C:38]([N+:40]([O-])=O)[CH:37]=[CH:36][C:20]=1[C:21]([O:23][CH:24]1[CH:30]([OH:31])[C:29]([CH3:33])([CH3:32])[CH2:28][C:27](=[O:34])[C:26]([CH3:35])=[CH:25]1)=[O:22])([O-])=O.[N+](C1C=C([N+]([O-])=O)C=CC=1C(OC1C(C)(C)CC(=O)C(C)=CC1O)=O)([O-])=O>CCCCCC.C(OCC)(=O)C>[NH2:16][C:19]1[CH:39]=[C:38]([NH2:40])[CH:37]=[CH:36][C:20]=1[C:21]([O:23][CH:24]1[CH:30]([OH:31])[C:29]([CH3:33])([CH3:32])[CH2:28][C:27](=[O:34])[C:26]([CH3:35])=[CH:25]1)=[O:22]

Participants

5

Reactant 3

HCID 118802,4-Dinitrobenzoic acidHCID 22922342HCID 22922342, compoundHCID 22922377HCID 22922377, compound

Product 1

HCID 22922379HCID 22922379, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Saishin N (3.68 g, 20 mM) was treated with 2,4-dinitrobenzoic acid (6.79 g, 32 mM) according to the procedures described in Example 20, forming a mixture of 4-(2,4-dinitrobenzoyloxy)-5-hydroxy-2,6,6-trimethyl-2-cyclohepten-1-one and (per acyl transfer reaction) 5-(2,4-dinitrobenzoyloxy)-4-hydroxy-2,6,6-trimethyl-2-cyclohepten-1-one, and then the mixture was reduced at the nitro groups according to the procedures described in Example 19 and fractionated by silica gel column chromatography using hexane-ethyl acetate (3:2) as an eluent. The first eluted portion was crystallized from a mixed solution of ethyl acetate and hexane to obtain 1.65 g (26%) of 4-(2,4-diaminobenzoyloxy)-5-hydroxy-2,6,6-trimethyl-2-cyclohepten-1-one (AU242) as a brown powder. Melting point: 154° to 156° C.

Workup

  1. customforming
  2. customThe first eluted portion was crystallized from a mixed solution of ethyl acetate and hexane

Sources & evidence

ORD record
ord-542d55a28a284f3fa07c593db28bfd93
Source dataset
uspto-grants-1997_08
Patent number
US05661166

Reaction notes

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