Hydrochloric Acid → 2-[N'-(2,3-dibromo-8-oxo-5,6,7,8-tetrahydro-1H-pyrrolo[2,3-c]azepin-4-ylidene)-hydrazino]-benzoic acid

HRID 2234776Notes

Reaction equation

HRID 2234776 reaction equation
[Br:1][C:2]1[NH:13][C:5]2[C:6](=[O:12])[NH:7][CH2:8][CH2:9][C:10](=O)[C:4]=2[C:3]=1[Br:14].[NH:15]([C:17]1[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=1[C:19]([OH:21])=[O:20])[NH2:16].Cl>CCO.CC(O)C>[Br:1][C:2]1[NH:13][C:5]2[C:6](=[O:12])[NH:7][CH2:8][CH2:9][C:10](=[N:16][NH:15][C:17]3[CH:25]=[CH:24][CH:23]=[CH:22][C:18]=3[C:19]([OH:21])=[O:20])[C:4]=2[C:3]=1[Br:14]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 792232-Hydrazinobenzoic acidHCID 686372062,3-dibromo-6,7-dihydro-1H,5H-pyrrolo[2,3-c]azepine-4,8-dione

Product 1

HCID 1363421102-[N'-(2,3-dibromo-8-oxo-5,6,7,8-tetrahydro-1H-pyrrolo[2,3-c]azepin-4-ylidene)-hydrazino]-benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3776IsopropanolSolvent

Procedure

To a solution of 2,3-dibromo-6,7-dihydro-1H,5H-pyrrolo[2,3-c]azepine-4,8-dione (32.2 mg, 0.10 mmol) in EtOH (5 mL) is added 2-hydrazinobenzoic acid (22.6 mg, 0.12 mmol) and HCl in i-PrOH (6N, 0.3 mL). The mixture is refluxed for 2 hours and then concentrated under reduced pressure. The residue is purified by HPLC (C18 column, eluted with CH3CN/H2O with 0.05% TFA) to give 2-[N′-(2,3-dibromo-8-oxo-5,6,7,8-tetrahydro-1H-pyrrolo[2,3-c]azepin-4-ylidene)-hydrazino]-benzoic acid; 1H NMR (DMSO-d6) δ 2.80-2.86 (m, 2H), 3.30-3.34 (m, 2H), 6.82 (t, 1H, J=8.0 Hz), 7.51 (d, 1H, J=7.2 Hz), 7.83-7.88 (m, 2H), 8.13 (t, 1H, J=6.0 Hz), 11.03 (s, 1H), 12.95 (s, 1H), 13.13 (s, 1H); m/z [M++1] 456.9.

Workup

  1. temperatureThe mixture is refluxed for 2 hours
  2. concentrationconcentrated under reduced pressure
  3. customThe residue is purified by HPLC (C18 column, eluted with CH3CN/H2O with 0.05% TFA)

Sources & evidence

ORD record
ord-e1772d78d47c4b4cb00665cb7ba0536a
Source dataset
uspto-grants-2010_05
Patent number
US07713958B2

Reaction notes

Loading…