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

HRID 983933Notes

Reaction equation

HRID 983933 reaction equation
C[O:2][C:3](=O)[C:4]([C:6]1[C:16]2=[C:17]3[C:12](=[CH:13][CH:14]=[CH:15]2)[CH2:11][CH2:10][CH2:9][N:8]3[CH:7]=1)=[O:5].[OH-].[NH4+:20]>O1CCCC1>[C:6]1([C:4](=[O:5])[C:3]([NH2:20])=[O:2])[C:16]2=[C:17]3[C:12](=[CH:13][CH:14]=[CH:15]2)[CH2:11][CH2:10][CH2:9][N:8]3[CH:7]=1.[C:6]1([CH2:4][C:3]([NH2:20])=[O:2])[C:16]2=[C:17]3[C:12](=[CH:13][CH:14]=[CH:15]2)[CH2:11][CH2:10][CH2:9][N:8]3[CH:7]=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 86590434(5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)acetamide (5,6-Dihydro-4H-pyrrolo[3,2,1-ij]quinolin-1-yl)oxoacetamideYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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. was added concentrated ammonium hydroxide (2 mL). The bath was removed and the mixture stirred 3 hours. After diluting with 20 mL of water, the suspension was filtered, washed with 10 mL of water followed by 10 mL of diethyl ether, and dried under reduced pressure to provide 0.403 g (86%) of the desired compound as a light yellow solid.

Workup

  1. customThe bath was removed
  2. additionAfter diluting with 20 mL of water
  3. filtrationthe suspension was filtered
  4. washwashed with 10 mL of water
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-a09310600acd4645afe160ae28434131
Source dataset
uspto-grants-2005_03
Patent number
US06867198B2

Reaction notes

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