Toluene → HCID 19610408, compound

HRID 1602113Notes

Reaction equation

HRID 1602113 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1/[CH:10]=[CH:11]/[CH:12]=[C:13](\[O:17][CH3:18])/[C:14]([O-:16])=O.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C[Al](C)C.C1(C)C=CC=CC=1>>[CH2:19]([NH:26][C:14](=[O:16])/[C:13](/[O:17][CH3:18])=[CH:12]/[CH:11]=[CH:10]/[C:2]1[NH:1][C:9]2[C:4]([CH:3]=1)=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 1140TolueneHCID 7504BenzylamineHCID 16682925TrimethylaluminumHCID 19610386HCID 19610386, compound

Product 1

HCID 19610408HCID 19610408, compoundYield 32.4%

Procedure

This compound was prepared following the same procedure of Example 9 and starting from (2Z,4E)-5-(2-indolyl)-2-methoxy-2,4 pentadienoate (0.1 g, 0.39 mmol), benzylamine (0.043 ml, 0.39 mmol) and a solution of 2M trimethylaluminium in toluene (0.4 ml, 0.8 mmol). After crystallisation from isopropanol, 42 mg (32.4%) of the title compound were obtained, m.p.=204-205° C. 1H-NMR (acetone-d6): 10.55 (br s, 1H); 7.94 (br t, 1H); 7.51 (d, 1H); 7.38-7.21 (m, 6H); 7.18 (dd, 1H); 7.11 (ddd, 1H); 6.99 (ddd, 1H); 6.91 (d, 1H); 6.85 (d, 1H); 6.61 (s, 1H); 4.50 (d, 2H); 3.79 (s, 3H).

Workup

  1. customThis compound was prepared
  2. customAfter crystallisation from isopropanol

Sources & evidence

ORD record
ord-3015dfc8fd0f49ca8fdb38f8cb88980d
Source dataset
uspto-grants-1999_11
Patent number
US05981525

Reaction notes

Loading…