Levulinic Acid → HCID 86734554, compound

HRID 597050

Reaction equation

HRID 597050 reaction equation
[CH3:1][C:2]([CH2:4][CH2:5][C:6]([OH:8])=[O:7])=[O:3].Cl.[Cl:10][C:11]1[CH:20]=[C:19]2[C:14]([C:15]([N:21]([C:25]3[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][CH:26]=3)N=CC)=[N:16][CH:17]=[N:18]2)=[CH:13][CH:12]=1>O>[OH2:3].[CH3:1][C:2]1[N:21]([C:15]2[C:14]3[C:19](=[CH:20][C:11]([Cl:10])=[CH:12][CH:13]=3)[N:18]=[CH:17][N:16]=2)[C:25]2[C:26]([C:4]=1[CH2:5][C:6]([OH:8])=[O:7])=[CH:27][C:28]([O:31][CH3:32])=[CH:29][CH:30]=2

Participants

4

Reactant 2

HCID 11579Levulinic AcidHCID 86734555acetaldehyde N1-(7-chloroquinazolin-4-yl)p-methoxyphenylhydrazone hydrochloride

Product 1

HCID 86734554HCID 86734554, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of laevulinic acid (15g.) and acetaldehyde N1 -(7-chloroquinazolin-4-yl)-p-methoxyphenylhydrazone hydrochloride (3.3g.) was heated at 95°-100° C. for 18 hours. The mixture was poured into water (ca 300ml.), and the precipitated pale yellow solid was collected by filtration and dissolved in a mixture of water (80ml.) and ammonia solution (specific gravity 0.88, ca 5ml.). The solution was washed with ethyl acetate (2 × 25ml.). Addition of sodium chloride (ca 10g.) to the aqueous phase caused a yellow solid to precipitate. This was collected by filtration, and then dissolved in water. The solution was acidified with glacial acetic acid until precipitation was complete. The mixture was filtered to give, as solid residue, 2-methyl-5-methoxy-1-(7-chloroquinazolin-4-yl)indol-3-ylacetic acid monohydrate, m.p. 98°-100° C.

Workup

  1. temperaturewas heated at 95°-100° C. for 18 hours
  2. filtrationthe precipitated pale yellow solid was collected by filtration
  3. dissolutiondissolved in a mixture of water (80ml.) and ammonia solution (specific gravity 0.88, ca 5ml.)
  4. washThe solution was washed with ethyl acetate (2 × 25ml.)
  5. additionAddition of sodium chloride (ca 10g.) to the aqueous phase
  6. customto precipitate
  7. filtrationThis was collected by filtration
  8. dissolutiondissolved in water
  9. customThe solution was acidified with glacial acetic acid until precipitation
  10. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-157e2c242f784cbaac7562b73481385d
Source dataset
uspto-grants-1977_03
Patent number
US04012513

Linked notes

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