Hydrochloric Acid → 5-bromo-2-formyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide

HRID 1811136Notes

Reaction equation

HRID 1811136 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([C:18](N(OC)C)=[O:19])[CH2:8][C:9]=1[NH:10]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].Cl>C1COCC1>[Br:1][C:2]1[CH:14]=[CH:13][C:12]([C:15]([NH2:17])=[O:16])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH:7]([CH:18]=[O:19])[CH2:8][C:9]=1[NH:10]2

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 21226445Aluminium lithium hydride2×HCID 86642957HCID 86642957, compound

Product 1

HCID 866429585-bromo-2-formyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Step 2 A suspension of 5-bromo-N2-methoxy-N2-methyl-2,3,4,9-tetrahydro-1H-carbazole-2,8-dicarboxamide (1.73 g, 4.55 mmol) in THF (40 mL) was treated with lithium aluminum hydride (0.259 g, 6.82 mmol) portionwise over 30 min at 0° C. After 20 min, more lithium aluminum hydride (120 mg) was added portionwise, and the mixture was stirred at rt for 20 min. The reaction mixture was cooled to 0° C. and treated dropwise with 0.5 M hydrochloric acid, and the resulting mixture was extracted three times with DCM. The combined organic phases were washed with NaHCO3 (aq) and water, dried and concentrated to provide 5-bromo-2-formyl-2,3,4,9-tetrahydro-1H-carbazole-8-carboxamide as a yellow solid (1.31 g, 90%), used without further purification. Mass spectrum m/z 321, 323 (M+H)+.

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. extractionthe resulting mixture was extracted three times with DCM
  3. washThe combined organic phases were washed with NaHCO3 (aq) and water
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-199455d366354e5aa5c5e4be63dd9419
Source dataset
uspto-grants-2013_01
Patent number
US08362065B2

Reaction notes

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