Hydrochloric Acid → 1H-Indole-2-carboxylic acid, 4,5,6,7-tetrahydro-3-hydroxy-, ethyl ester

HRID 1447132Notes

Reaction equation

HRID 1447132 reaction equation
C([O:3][C:4]([C:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]=1[NH:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=O)C.[Na].O.Cl>C(O)C>[CH2:17]([O:16][C:14]([C:13]1[NH:12][C:7]2[CH2:8][CH2:9][CH2:10][CH2:11][C:6]=2[C:4]=1[OH:3])=[O:15])[CH3:18]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 585944HCID 585944, compoundHCID 5360545Sodium

Product 1

HCID 5961211H-Indole-2-carboxylic acid, 4,5,6,7-tetrahydro-3-hydroxy-, ethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

294 g of 2-(ethoxycarbonylmethylamino)-cyclohexene-1-carboxylic acid ethyl ester in 400 ml of ethanol are added dropwise, under nitrogen, to a well-stirred solution of 35 g of sodium in 1.5 liters of ethanol. After the solution has boiled for three hours, it is cooled and 600 ml of water are then added, followed by 150 ml of concentrated hydrochloric acid. After the batch has stood for six hours at -10° C., 142 g of 3-hydroxy-4,5,6,7-tetrahydroindole-2-carboxylic acid ethyl ester, of melting point 94°-95° C., are filtered off.

Workup

  1. temperatureit is cooled
  2. waitAfter the batch has stood for six hours at -10° C.
  3. filtration142 g of 3-hydroxy-4,5,6,7-tetrahydroindole-2-carboxylic acid ethyl ester, of melting point 94°-95° C., are filtered off

Sources & evidence

ORD record
ord-0b7f569216dc4c35944a25470a773c62
Source dataset
uspto-grants-1982_02
Patent number
US04315939

Reaction notes

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