Hydrochloric Acid → 5-Nitroindoline-7-carboxylic acid

HRID 4930Notes

Reaction equation

HRID 4930 reaction equation
Cl.C([N:5]1[C:13]2[C:8](=[CH:9][C:10]([N+:16]([O-:18])=[O:17])=[CH:11][C:12]=2[C:14]#N)[CH2:7][CH2:6]1)(=O)C.[OH-:19].[Na+].[OH2:21]>>[N+:16]([C:10]1[CH:9]=[C:8]2[C:13](=[C:12]([C:14]([OH:21])=[O:19])[CH:11]=1)[NH:5][CH2:6][CH2:7]2)([O-:18])=[O:17]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 19797206N-Acetyl-7-cyano-5-nitroindoline

Product 1

HCID 197972125-Nitroindoline-7-carboxylic acidYield 77.1%

Conditions

Temperature
140 °C

Procedure

Into concentrated hydrochloric acid (63.6 ml) was dissolved N-acetyl-7-cyano-5-nitroindoline (5.3 g), which was then subjected to stirring at 140° C. for 45 minutes. The reaction mixture was cooled to 0° C. to give deposited crystal, which was then collected by filtration. The obtained crude crystal was suspended into water (50 ml), and was rendered basic by adding 50% sodium hydroxide, and the insoluble matter was collected by filtration. After adding concentrated hydrochloric acid to the filtrate, the deposited crystal was collected by filtration and dried to give the intended compound 3.7 g (77.1%) as yellow powder. M.P.: 294°-297° C. (decomp.)

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customto give
  3. filtrationwas then collected by filtration
  4. customThe obtained crude crystal
  5. filtrationthe insoluble matter was collected by filtration
  6. additionAfter adding concentrated hydrochloric acid to the filtrate
  7. filtrationthe deposited crystal was collected by filtration
  8. customdried

Sources & evidence

ORD record
ord-00fe2cb189c24e55aa0d927376670bed
Source dataset
uspto-grants-1993_09
Patent number
US05242912

Reaction notes

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