5-Methylfurfural → HCID 55081698, compound

HRID 2116724Notes

Reaction equation

HRID 2116724 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](N)([NH:11][CH3:12])[CH:6]([CH:10]=1)[C:7]([O-:9])=[O:8].C(NC1C=CC(C(O)=O)=C(N[CH2:28][C:29]2[O:30][CH:31]=[CH:32][CH:33]=2)C=1)(=O)C.CC1OC(C=O)=CC=1>ClCCCl.C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([NH:11][CH2:12][C:31]2[O:30][C:29]([CH3:28])=[CH:33][CH:32]=2)=[C:6]([CH:10]=1)[C:7]([OH:9])=[O:8]

Participants

6

Reactant 3

HCID 120975-MethylfurfuralHCID 59814776HCID 59814776, compoundHCID 86594330HCID 86594330, compound

Product 1

HCID 55081698HCID 55081698, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Reductive amination of 5-chloro-2-amino-methylanthranilate carried out as described for compound 1 using 5-methyl furaldehyde in DCE for 4 hrs. After workup, the product was isolated by FC using 10-30% acetone/hexanes to afford a light yellow solid. The ester was subsequently taken up in THF and saponified using 1N at 60° C. for 12 hrs. The solution was cooled, acidified and the product collected as an off-white solid.

Workup

  1. customAfter workup, the product was isolated by FC
  2. customto afford a light yellow solid
  3. customat 60° C.
  4. customfor 12 hrs
  5. temperatureThe solution was cooled
  6. customthe product collected as an off-white solid

Sources & evidence

ORD record
ord-f76ebc2c7f054b3c98530a8abbec1646
Source dataset
uspto-grants-2008_10
Patent number
US07439249B2

Reaction notes

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