Hydrochloric Acid → HCID 21714323, compound

HRID 1600627Notes

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

Conditions

Temperature: 72.5 °C

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

temperatureThe reaction mixture was cooled to room temperature
extractionfollowed by extraction with ethyl acetate (twice)
extractionSubsequently, the organic layer was extracted with aqueous ammonia (prepared from 130 ml of 28% aqueous ammonia and 100 ml of water)
customthe aqueous layer thus obtained
customThe solid precipitated
filtrationwas collected by filtration
washwashed with water
customdried under reduced pressure

Sources & evidence

ORD record: ord-6a5897bcb5bd402a8f47c87212fc66e4
Source dataset: uspto-grants-1999_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05977100

Reaction notes

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