Hydrochloric Acid → HCID 68424025, compound

HRID 1873669Notes

Reaction equation

HRID 1873669 reaction equation
C(OC(=O)[NH:7][CH2:8][C:9]([C:11]1[C:21]2=[C:22]3[C:17](=[CH:18][CH:19]=[CH:20]2)[CH2:16][CH2:15][CH2:14][N:13]3[CH:12]=1)=[O:10])(C)(C)C.[ClH:24]>C(Cl)Cl>[ClH:24].[NH2:7][CH2:8][C:9]([C:11]1[C:21]2=[C:22]3[C:17](=[CH:18][CH:19]=[CH:20]2)[CH2:16][CH2:15][CH2:14][N:13]3[CH:12]=1)=[O:10]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59404395HCID 59404395, compound

Product 1

HCID 68424025HCID 68424025, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-2-oxo-ethyl]-carbamic acid tert-butyl ester (1.35 g, 4.30 mmol) in DCM (50 mL) was added HCl (4 M in dioxane, 11 mL, 44 mmol) at room temperature. The reaction mixture was stirred for 2 hours at room temperature. The precipitate formed was filtered through a filter paper, washed with DCM and dried under vacuum to give 2-amino-1-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-ethanone HCl salt (1.06 g, 99%) as a white solid. 1H NMR (400 MHz, CDCl3) δ: 8.50 (s, 1H), 8.42 (brs, 3H), 7.88 (d, J=8.0 Hz, 1H), 7.20 (m, 1H), 7.03 (d, J=8.0 Hz, 1H), 4.28 (m, 4H), 2.95 (t, J=5.6 Hz, 2H), 2.15 (m, 2H). LCMS: m/e 215.21 [M+H].

Workup

  1. customThe precipitate formed
  2. filtrationwas filtered through a filter paper
  3. washwashed with DCM
  4. customdried under vacuum

Sources & evidence

ORD record
ord-e47bd88105af4eeb90c8bbc766a2905d
Source dataset
uspto-grants-2012_11
Patent number
US08304425B2

Reaction notes

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