Hydrochloric Acid → 8-Bromo-5-aminomethyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione hydrochloride

HRID 52470Notes

Reaction equation

HRID 52470 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([CH2:16][N:17]3C(=O)C4=CC=CC=C4C3=O)[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23.[ClH:28]>C(O)(=O)C>[ClH:28].[Br:1][C:2]1[CH:3]=[C:4]2[CH2:15][CH:14]([CH2:16][NH2:17])[N:6]3[C:7](=[O:13])[C:8](=[O:12])[NH:9][C:10]([CH:11]=1)=[C:5]23

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 104551318-bromo-5-phthalimidomethyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione

Product 1

HCID 199632338-Bromo-5-aminomethyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione hydrochlorideYield 60%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 8-bromo-5-phthalimidomethyl-5,6-dihydro-1H-pyrrolo[1,2,3-de]quinoxaline-2,3-dione (100 mg)in a mixture of acetic acid (6 mL) and concentrated HCl (6 mL) was refluxed for 4.5 h and concentrated. The residue was triturated with methylenechloride containing a small amount of methanol. The precipitates were collected by filtration, rinsed with methylenechloride, and dried in vacuo to give 60 mg of the title compound (60%): mp 268° C. (dec); 1H NMR (270 MHz, DMSO-d6) δ11.98 (s, 1H), 8.07 (br, 3H), 7.23 (d, 1H, J=1 Hz), 7.07 (d, 1H, J=1 Hz), 5.02~5.12 (m, 1H), 3.56 (dd, 1H, J=17, 10 Hz), 3.28~3.48 (m, 2H), 3.11 (dd, 1H, J=17, 3 Hz).

Workup

  1. temperaturewas refluxed for 4.5 h
  2. concentrationconcentrated
  3. customThe residue was triturated with methylenechloride containing a small amount of methanol
  4. filtrationThe precipitates were collected by filtration
  5. washrinsed with methylenechloride
  6. customdried in vacuo

Sources & evidence

ORD record
ord-bb6f61fddc914c4ba64e40d4fa56663b
Source dataset
uspto-grants-1997_04
Patent number
US05616586

Reaction notes

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