7-Benzyloxy-6-cyano-4-(1H-indol-5-yloxy)quinoline → 6-Cyano-4-(1H-indol-5-yloxy)-7-hydroxyquinoline

HRID 1010262Notes

Reaction equation

HRID 1010262 reaction equation
C([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[NH:25][CH:24]=[CH:23]4)=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[C:29]#[N:30])C1C=CC=CC=1>O1CCCC1.[C].[Pd]>[C:29]([C:10]1[CH:11]=[C:12]2[C:17](=[CH:18][C:9]=1[OH:8])[N:16]=[CH:15][CH:14]=[C:13]2[O:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[CH:23]2)#[N:30]

Participants

4

Reactant 1

HCID 229364817-Benzyloxy-6-cyano-4-(1H-indol-5-yloxy)quinoline

Product 1

HCID 1358293896-Cyano-4-(1H-indol-5-yloxy)-7-hydroxyquinolineYield 79.12%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalyst3×HCID 8028TetrahydrofuranSolvent

Procedure

After dissolving 7-benzyloxy-6-cyano-4-(1H-indol-5-yloxy)quinoline (3 g, 7.6642 mmol) in tetrahydrofuran (250 ml), 10% palladium carbon powder (500 mg, wet) was added and the mixture was stirred for 11 hours at room temperature under a hydrogen atmosphere. After further adding 10% palladium carbon powder (300 mg, wet) and stirring the mixture for 9 hours at room temperature under a hydrogen atmosphere, additional 10% palladium carbon powder (200 mg, wet) was added and the mixture was stirred for 5 hours at room temperature under a hydrogen atmosphere. The solvent was distilled off, washing was performed with ethanol, and then the filtrate was distilled off under reduced pressure. The obtained crystals were suspended in ethanol and diluted with hexane, and the crystals were filtered out, washed with hexane:ethanol=3:1 and dried by aspiration to obtain the title compound (1.82 g, 6.0402 mmol, 79.12%) as light yellow crystals.

Workup

  1. additionwas added
  2. stirringstirring the mixture for 9 hours at room temperature under a hydrogen atmosphere
  3. stirringthe mixture was stirred for 5 hours at room temperature under a hydrogen atmosphere
  4. distillationThe solvent was distilled off
  5. washwashing
  6. distillationthe filtrate was distilled off under reduced pressure
  7. additiondiluted with hexane
  8. filtrationthe crystals were filtered out
  9. washwashed with hexane
  10. dry with materialethanol=3:1 and dried by aspiration

Sources & evidence

ORD record
ord-352ab5564b48433bbc0782d32b344015
Source dataset
uspto-grants-2011_07
Patent number
US07973160B2

Reaction notes

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