4-Nitrobenzaldehyde → 1-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-beta-carboline

HRID 1637868Notes

Reaction equation

HRID 1637868 reaction equation
[NH2:1][CH2:2][CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1.[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]=O)=[CH:18][CH:17]=1)([O-:15])=[O:14].C(O)(C(F)(F)F)=O>>[N+:13]([C:16]1[CH:23]=[CH:22][C:19]([CH:20]2[C:5]3[NH:6][C:7]4[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:4]=3[CH2:3][CH2:2][NH:1]2)=[CH:18][CH:17]=1)([O-:15])=[O:14]

Participants

4

Reactant 3

HCID 5414-NitrobenzaldehydeHCID 1150TryptamineHCID 6422Trifluoroacetic acid

Product 1

HCID 34742861-(4-nitrophenyl)-2,3,4,9-tetrahydro-1H-beta-carbolineYield 86%

Procedure

This product was prepared using the same procedure as for Intermediate 1 with tryptamine (2.0 g, 12.5 mmol), 4-nitrobenzaldehyde (1.88 g, 1 equiv.) and TFA (1.9 mL, 2 equiv.) to give the title compound (3.1 g, 86%) as a yellow powder. MP: 190° C.

Workup

  1. customThis product was prepared

Sources & evidence

ORD record
ord-0e0ff14c25e8451eae3aafd631587e78
Source dataset
uspto-grants-2000_03
Patent number
US06043252

Reaction notes

Loading…