HCID 492201, compound → HCID 492202, compound

HRID 2379064Notes

Reaction equation

HRID 2379064 reaction equation
[N:1]([C:4]1[N:8]([C@@H:9]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:11]([OH:12])[CH2:10]2)[C:7]2[CH:17]=[C:18]([Cl:22])[C:19]([Cl:21])=[CH:20][C:6]=2[N:5]=1)=[N+]=[N-]>CCO.[Ni]>[NH2:1][C:4]1[N:8]([C@@H:9]2[O:14][C@H:13]([CH2:15][OH:16])[C@@H:11]([OH:12])[CH2:10]2)[C:7]2[CH:17]=[C:18]([Cl:22])[C:19]([Cl:21])=[CH:20][C:6]=2[N:5]=1

Participants

4

Reactant 1

HCID 492201HCID 492201, compound

Product 1

HCID 492202HCID 492202, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of 110b (1.032 g, 3 mmol) and Ra-Ni (0.24 g, wet) in 30 mL of EtOH was hydrogenated (50 psi of H2) at room temperature for 6 Hr. The reaction mixture was filtered and the filtrate was evaporated. The residue was suspended in 20 mL of MeCN and the suspension was filtered to give 0.856 g (90%, 2 crops) of 113 as a white solid. Analytical sample (as white needles) was obtained by recrystallization from MeOH/MeCN. MP: 216°-221° C. (dec.). MS: (El) m/e 317.0340 (37%, M+ =317.0334). 1H NMR (DMSO-d6): d 7.71 (s, 1, 7-H), 7.29 (s, 1, 4-H), 6.93 (br s, 2, 2-NH2), 6.23 (dd, 1, 1'-H, J1'-2' =8.5 Hz, J1'-2" =6.0 Hz), 5.40 (t, 1, 5'-OH, J5' -5'OH =4.5 Hz), 5.34 (d, 1, 3'-OH, J3'-3'OH= 4.0 Hz), 4.40 (m, 1, 3'-H, J3'-2' =7.0 Hz, J3'-2" =2.0 Hz, J3'-4' =2.5 Hz), 3.82 (m, 1, 4'-H, J4'-5' =2.5 Hz), 3.68 (m, 2,5'-H), 2.40 (m, 1, 2'-H, J2'-2" =13.0 Hz), 2.05 (m, 1, 2"-H). 13C NMR (DMSO-d6): d 155.85 (C2), 143.16 (C3a), 132.40 (C7a), 122.94, 119.77 (C5 and C6), 115.35 (C4), 110.69 (C7), 86.91 (C4'), 83.87 (C1'), 70.20 (C3'), 60.74 (C5'), 38.05 (C2'). Anal. Calcd. for C12H13Cl2N3O3 : C, 45.30; H, 4.12; N, 13.21. Found: C, 45.44; H, 4.10; N, 13.28.

Workup

  1. customat room temperature
  2. filtrationThe reaction mixture was filtered
  3. customthe filtrate was evaporated
  4. filtrationthe suspension was filtered

Sources & evidence

ORD record
ord-66867a2ac88d42458a62922f2a48a1df
Source dataset
uspto-grants-1994_11
Patent number
US05360795

Reaction notes

Loading…