Carbamide Peroxide → HCID 67094191, compound

HRID 2403666Notes

Reaction equation

HRID 2403666 reaction equation
C([O:3][C:4]([C:6]1[CH:14]=[C:13]2[C:9]([C:10]([C:15]#[N:16])=[CH:11][NH:12]2)=[CH:8][CH:7]=1)=[O:5])C.OO.NC(N)=[O:21]>CO.[OH-].[Na+]>[C:15]([C:10]1[C:9]2[C:13](=[CH:14][C:6]([C:4]([OH:3])=[O:5])=[CH:7][CH:8]=2)[NH:12][CH:11]=1)(=[O:21])[NH2:16]

Participants

5

Reactant 2

HCID 31294Carbamide Peroxide2×HCID 70896148HCID 70896148, compound

Product 1

HCID 67094191HCID 67094191, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 14798Sodium HydroxideSolvent2×

Procedure

A suspension of 3-cyano-1H-indole-6-carboxylic acid ethyl ester (100 mg, 1.4 mmol) in methanol (1.12 mL) was added to a solution of urea hydrogen peroxide (453 mg, 4.67 mmol) in 2.5 M sodium hydroxide (1.12 mL, 2.80 mmol) at 0° C. The suspension was allowed to warm to room temperature and was stirred overnight. The reaction was concentrated under reduced pressure. Water was added and the solution was acidified with 3 N aqueous hydrochloric acid to pH=2. A precipitate formed. The reaction mixture was stirred for 1 minute at room temperature and was then filtered to give an orange solid. Additional urea hydrogen peroxide (453 mg) in 2.5 M sodium hydroxide and methanol was added and the mixture was stirred for 2 hours. The reaction was concentrated, diluted with water, acidified to pH=3 and filtered. The solid was washed with water and heptanes and was dried in a vacuum oven to give 3-carbamoyl-1H-indole-6-carboxylic acid as a solid (66.5 mg, 70%). −ESI (M−1) 203.1; 1H NMR (400 MHz, DMSO-d6, δ): 12.45 (br. s., 1 H), 11.78 (br. s., 1 H), 8.83 (d, J=1.6 Hz, 1 H), 8.09 (d, J=2.9 Hz, 1 H), 7.73 (dd, J=8.6, 1.8 Hz, 1 H), 7.51 (br. s., 1 H), 7.45 (d, J=8.4 Hz, 1 H), 6.89 (br. s., 1 H).

Workup

  1. concentrationThe reaction was concentrated under reduced pressure
  2. additionWater was added
  3. customA precipitate formed
  4. stirringThe reaction mixture was stirred for 1 minute at room temperature
  5. filtrationwas then filtered
  6. customto give an orange solid
  7. stirringthe mixture was stirred for 2 hours
  8. concentrationThe reaction was concentrated
  9. additiondiluted with water
  10. filtrationfiltered
  11. washThe solid was washed with water and heptanes
  12. customwas dried in a vacuum oven

Sources & evidence

ORD record
ord-712fa484985942c0818818a4400e2f97
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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