Hydrochloric Acid → HCID 22556762, compound

HRID 1894742Notes

Reaction equation

HRID 1894742 reaction equation
C([O:3][C:4]([C:6]1[N:7]2[CH2:16][CH2:15][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([CH:14]=1)[C:8]2=3)=[O:5])C.O.Cl>C(O)C.[OH-].[Na+]>[CH:14]1[C:13]2[C:8]3=[C:9]([CH2:15][CH2:16][N:7]3[C:6]=1[C:4]([OH:5])=[O:3])[CH:10]=[CH:11][CH:12]=2

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 13477702HCID 13477702, compound

Product 1

HCID 22556762HCID 22556762, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 4,5-dihydro-pyrrolo[3,2,1-hi]indole-2-carboxylic acid ethyl ester (1.117 g) in ethanol (25 ml) and 2M sodium hydroxide (25 ml) was heated to reflux for 1 hour. The mixture was cooled to room temperature and poured into water (300 ml). 1M hydrochloric acid was added until pH1 and the precipitate formed filtered off and washed with water (50 ml). After drying under reduced pressure 4,5-dihydro-pyrrolo[3,2,1-hi]indole-2-carboxylic acid was obtained as a pale yellow powder (884 mg). 400 MHz 1H NMR (DMSO-d6) δ: 12.94 (s, 1H), 7.31 (d, J=7.2 Hz, 1H), 7.01-6.96 (m, 3H), 4.67 (t, J=6.8 Hz, 2H), 3.74 (t, J=6.8 Hz, 2H); LCMS: 188 [M+H].

Workup

  1. temperatureto reflux for 1 hour
  2. customthe precipitate formed
  3. filtrationfiltered off
  4. washwashed with water (50 ml)
  5. dry with materialAfter drying under reduced pressure 4,5-dihydro-pyrrolo[3,2,1-hi]indole-2-carboxylic acid

Sources & evidence

ORD record
ord-760df26c9350482080ea27f9cc6d4996
Source dataset
uspto-grants-2013_08
Patent number
US08513292B2

Reaction notes

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