Water → HCID 178512784, compound

HRID 1459629Notes

Reaction equation

HRID 1459629 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:35]=[CH:36][CH:37]=1)[CH2:5][N:6]1[C:11]2[CH:12]=[C:13]([N+:16]([O-])=O)[CH:14]=[CH:15][C:10]=2[O:9][CH:8]([CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][CH2:29][NH:30][C:31]([NH2:33])=[NH:32])=[CH:24][CH:23]=2)[C:7]1=[O:34].O.[NH4+].[Cl-]>C(O)C.[Fe]>[NH2:16][C:13]1[CH:14]=[CH:15][C:10]2[O:9][CH:8]([CH2:19][CH2:20][O:21][C:22]3[CH:23]=[CH:24][C:25]([CH2:28][CH2:29][NH:30][C:31]([NH2:33])=[NH:32])=[CH:26][CH:27]=3)[C:7](=[O:34])[N:6]([CH2:5][C:4]3[CH:35]=[CH:36][CH:37]=[C:2]([Cl:1])[CH:3]=3)[C:11]=2[CH:12]=1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 178512785HCID 178512785, compound

Product 1

HCID 178512784HCID 178512784, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

4-(3-Chlorobenzyl)-3,4-dihydro-2-{2-[4-(2-guanidinoethyl)phenoxy]ethyl}-6-nitro-3-oxo-2H-1,4-benzoxazine (0.3 g) was warmed in ethanol (5 ml) and H2O (4 ml) until completely in solution. Iron powder (0.19 g, 6.8 eq) was stirred in followed by NH4Cl (0.02 g, 0.7 eq) and the reaction continued at reflux for 5 hours. While still hot, the mixture was filtered through celite and the yellow filtrate concentrated down to a yellow oil. After drying in vacuo at 80 C.°, the product was collected as a yellow solid in 85% yield, mp (dec)>94° C.; MS (Cl) MH+ 494; IR (KBr) 3332, 1667, 1614, 1512, 1467, 1396, 1243, 830, 774, 680 cm-1 ; 1H NMR (DMSO-d6 /CDCl3) δ 7.66 (br s, 1H), 7.58-6.50 (v br s, 3H), 7.36 (m, 4H), 7.20 (m, 3H), 6.91 (d, 2H, J=8.6 Hz), 6.74 (d, 1H, J=8.4 Hz), 6.26 (d, 1H, J=2.2 Hz), 6.21 (dd, 1H, J=2.2, 8.4 Hz), 5.08 (d, 1H, J=16.7 Hz), 4.99 (d, 1H, J=16.5 Hz), 5.12-4.78(v br s., 1H), 4.79 (dd, 1H, J=4.0, 8.9 Hz), 4.15 (m, 2H), 3.33 (m, 2H), 2.71 (t, 2H, J=7.5 Hz), 2.30 (m, 1H), 2.18 (m, 1H). Anal. Calc'd for C26H28ClN5O3.HCl.0.5 H2O: C 57.89, H 5.61, N 12.98. Found: C 57.64, H 5.48, N 12.63.

Workup

  1. temperatureat reflux for 5 hours
  2. filtrationWhile still hot, the mixture was filtered through celite
  3. concentrationthe yellow filtrate concentrated down to a yellow oil
  4. customAfter drying in vacuo at 80 C.°
  5. customthe product was collected as a yellow solid in 85% yield, mp (dec)>94° C.

Sources & evidence

ORD record
ord-6d52c26f039c48d096fd9d248d0d83e2
Source dataset
uspto-grants-1998_12
Patent number
US05854242

Reaction notes

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