Hydrochloric Acid → 7-Chloro-1-hydroxymethyl-8-methylcarbazole

HRID 1076183Notes

Reaction equation

HRID 1076183 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[Cl:12][C:13]1[C:25]([CH3:26])=[C:24]2[C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]([C:27](O)=[O:28])[C:22]=3[NH:23]2)=[CH:15][CH:14]=1.Cl>C(OCC)(=O)C>[Cl:12][C:13]1[C:25]([CH3:26])=[C:24]2[C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[C:21]([CH2:27][OH:28])[C:22]=3[NH:23]2)=[CH:15][CH:14]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028Tetrahydrofuran2×HCID 21226445Aluminium lithium hydrideHCID 213999317-Chloro-8-methylcarbazole-1-carboxylic acid

Product 1

HCID 213999347-Chloro-1-hydroxymethyl-8-methylcarbazoleYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A suspension of 0.3 g. of lithium aluminum hydride in 5 ml. of absolute tetrahydrofuran is combined dropwise with 0.560 g. of the ethyl ester of 7-chloro-8-methylcarbazole-1-carboxylic acid, dissolved in 10 ml. of absolute tetrahydrofuran; the mixture is agitated for one hour at room temperature. Then, the reaction mixture is heated for one hour under reflux, allowed to cool, diluted with 20 ml. of ethyl acetate, mixed under cooling dropwise with hydrochloric acid, and the organic phase is separated, washed, and concentrated under vacuum. The residue is recrystallized from toluene, thus obtaining, in a 95% yield, 7-chloro-1-hydroxymethyl-8-methylcarbazole, m.p. 187° C.

Workup

  1. additionA suspension of 0.3 g
  2. temperatureThen, the reaction mixture is heated for one hour
  3. temperatureunder reflux
  4. temperatureto cool
  5. additiondiluted with 20 ml
  6. customthe organic phase is separated
  7. washwashed
  8. concentrationconcentrated under vacuum
  9. customThe residue is recrystallized from toluene

Sources & evidence

ORD record
ord-85c2c1a5010546d0b0e8ffda6fb8abcb
Source dataset
uspto-grants-1976_05
Patent number
US03956295

Reaction notes

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