Methanol → 6-chloro-7-methoxy-8-nitro-9H-pyrido[3,4-b]indole

HRID 552174Notes

Reaction equation

HRID 552174 reaction equation
[CH3:1][OH:2].[H-].[Na+].[Cl:5][C:6]1[CH:7]=[C:8]2[C:16](=[C:17]([N+:20]([O-:22])=[O:21])[C:18]=1F)[NH:15][C:14]1[CH:13]=[N:12][CH:11]=[CH:10][C:9]2=1.O>CN(C=O)C>[Cl:5][C:6]1[CH:7]=[C:8]2[C:16](=[C:17]([N+:20]([O-:22])=[O:21])[C:18]=1[O:2][CH3:1])[NH:15][C:14]1[CH:13]=[N:12][CH:11]=[CH:10][C:9]2=1

Participants

6

Reactant 4

HCID 887MethanolHCID 962WaterHCID 24758Sodium hydrideHCID 593375336-chloro-7-fluoro-8-nitro-9H-pyrido[3,4-b]indole

Product 1

HCID 593375346-chloro-7-methoxy-8-nitro-9H-pyrido[3,4-b]indoleYield 97%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methanol (0.462 ml, 11.4 mmol) was added to a stirring suspension of NaH (684 mg, 17.1 mmol) in DMF (10 ml) under an argon atmosphere. The resulting solution was allowed to stir at RT for 20 min. 6-chloro-7-fluoro-8-nitro-9H-β-carboline (500 mg, 1.9 mmol) was added to the stirring solution and the resulting mixture was allowed to stir at RT. Upon addition of H2O, a brown solid precipitated out which was filtered to give the desired 6-chloro-7-methoxy-8-nitro-9H-β-carboline (510 mg, 97% yield). 1H-NMR (300 MHz, DMSO-d6): δ 4.02 (s, 3H), 8.52 (d, 1H), 8.60 (d, 1H), 9.05 (s, 1H), 9.12 (s, 1H), 12.78 (b, 1H). Retention Time (LC, method: ammonium acetate standard): 2.28 min. MS (M+H+): 278.

Workup

  1. stirringto stir at RT
  2. customa brown solid precipitated out which
  3. filtrationwas filtered

Sources & evidence

ORD record
ord-8ed048a6fd0c4ea5bfe720fd42d71238
Source dataset
uspto-grants-2011_05
Patent number
US07951801B2

Reaction notes

Loading…