Hydrochloric Acid → HCID 21714323, compound

HRID 355706Notes

Reaction equation

HRID 355706 reaction equation
C(O[CH:4]([C:22]([OH:24])=[O:23])[CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[C:11]([CH3:16])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])C.S(=O)(=O)(O)O.Cl>C(O)(=O)C>[C:22]([CH2:4][CH2:5][CH2:6][N:7]1[C:15]2[C:10](=[C:11]([CH3:16])[CH:12]=[CH:13][CH:14]=2)[CH:9]=[C:8]1[C:17]([O:19][CH2:20][CH3:21])=[O:18])([OH:24])=[O:23]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 1118Sulfuric AcidHCID 70238260HCID 70238260, compound

Product 1

HCID 21714323HCID 21714323, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 1-(3-ethoxycarboxypropyl)-4-methyl-1H-indole-2-carboxylate (15.4 g, 48.5 mmol), acetic acid (250 ml) and 30% sulfuric acid (125 ml) was stirred at 70°-75° C. for 1.5 hours. The reaction mixture was cooled to room temperature and then poured into ice water, followed by extraction with ethyl acetate (twice). Subsequently, the organic layer was extracted with aqueous ammonia (prepared from 130 ml of 28% aqueous ammonia and 100 ml of water), and the aqueous layer thus obtained was adjusted to pH 3 to 4 with 35% hydrochloric acid. The solid precipitated was collected by filtration, washed with water and then dried under reduced pressure to obtain 9.2 g of ethyl 1-(3-carboxypropyl)-4-methyl-1H-indole-2-carboxylate.

Workup

  1. extractionfollowed by extraction with ethyl acetate (twice)
  2. extractionSubsequently, the organic layer was extracted with aqueous ammonia (prepared from 130 ml of 28% aqueous ammonia and 100 ml of water)
  3. customthe aqueous layer thus obtained
  4. customThe solid precipitated
  5. filtrationwas collected by filtration
  6. washwashed with water
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-c20b73e646864d7fac6174b0889cb300
Source dataset
uspto-grants-1998_11
Patent number
US05834454

Reaction notes

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