HCID 19800643, compound → HCID 19800662, compound

HRID 1646449Notes

Reaction equation

HRID 1646449 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5]1[C:6](=[CH:12][C:13]([NH2:17])=[C:14]([OH:16])[CH:15]=1)[C:7]([O:9][CH2:10][CH3:11])=[O:8])[CH3:2].[CH2:19](C(CC)(CC)C([O-])([O-])[O-])[CH3:20]>>[CH3:19][C:20]1[O:16][C:14]2[CH:15]=[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:18])[C:6]([C:7]([O:9][CH2:10][CH3:11])=[O:8])=[CH:12][C:13]=2[N:17]=1

Participants

3

Reactant 2

HCID 19800643HCID 19800643, compoundHCID 21875354Triethylorthoaceate

Product 1

HCID 19800662HCID 19800662, compound

Procedure

A mixture of diethyl-4-amino-5-hydroxyphthalate (4.00 g, 15.8 mmol) and triethylorthoacetate (29.0 mL, 158 mmol) is stirred for 2 hours at reflux temperature, cooled to room temperature and diluted with hexanes. Silica gel chromatography (gradient elution:hexanes to (2:1) hexanes:ethyl acetate) followed by recrystallization from 1% ethyl acetate:-hexanes affords the title product as an off-white crystalline solid, 3.54 g (80.8%), identified by NMR, IR and mass spectral analyses.

Workup

  1. temperatureat reflux temperature
  2. washSilica gel chromatography (gradient elution:hexanes to (2:1) hexanes:ethyl acetate)
  3. customfollowed by recrystallization from 1% ethyl acetate

Sources & evidence

ORD record
ord-5adf0e52ce9649bbbb85070c75fe6c69
Source dataset
uspto-grants-1993_01
Patent number
US05180419

Reaction notes

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