Ammonium Hydroxide → (5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)Oxoacetamide

HRID 557189Notes

Reaction equation

HRID 557189 reaction equation
[OH-].[NH4+:2].C[O:4][C:5](=O)[C:6]([C:8]1[C:18]2=[C:19]3[C:14](=[CH:15][CH:16]=[CH:17]2)[CH2:13][CH2:12][CH2:11][N:10]3[CH:9]=1)=[O:7]>O1CCCC1>[C:8]1([C:6](=[O:7])[C:5]([NH2:2])=[O:4])[C:18]2=[C:19]3[C:14](=[CH:15][CH:16]=[CH:17]2)[CH2:13][CH2:12][CH2:11][N:10]3[CH:9]=1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 59298805methyl 2-(5,6-dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)-2-oxoacetate

Product 1

HCID 22556693(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)OxoacetamideYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Add concentrated ammonium hydroxide (2 mL) to a solution of (5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetic acid methyl ester (0.50 g, 2.06 mmol) in 10 mL of tetrahydrofuran at 0° C. Remove the cooling bath and stir the mixture for 3 hours. Dilute the reaction with 20 mL of water and filter the suspension. Wash the filter cake with 10 mL of water followed by 10 mL of diethyl ether, and dry under reduced pressure to provide the desired compound as a light yellow solid (0.403 g, 86%).

Workup

  1. customRemove the cooling bath
  2. additionDilute
  3. customthe reaction with 20 mL of water
  4. filtrationfilter the suspension
  5. washWash the filter cake with 10 mL of water
  6. customdry under reduced pressure

Sources & evidence

ORD record
ord-b17d3617b1c74c168301cd98de07dc53
Source dataset
uspto-grants-2011_11
Patent number
US08058425B2

Reaction notes

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