Ammonium Hydroxide → HCID 69235318, compound

HRID 1593638Notes

Reaction equation

HRID 1593638 reaction equation
[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH:3]([C:14]([OH:16])=O)[CH2:2]1.C(Cl)(=O)C(Cl)=O.[OH-].[NH4+:24]>C(Cl)Cl.CN(C=O)C>[CH2:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH2:4][CH:3]([C:14]([NH2:24])=[O:16])[CH2:2]1

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 13491214HCID 13491214, compound

Product 1

HCID 69235318HCID 69235318, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid (30.4 g, 141 mmol), was suspended in 450 ml of methylene chloride and cooled to 0° C. Oxalyl chloride (14.8 mL, 169 mmol) was added dropwise, followed by two drops of DMF. The resulting mixture was allowed to warm to room temperature and was stirred for 24 h. After re-cooling to 0° C., 450 mL of conc. aqueous ammonium hydroxide were added dropwise. The yellow precipitate that formed was collected by vacuum filtration. After drying, the title compound weighed 17.4 g (58%).

Workup

  1. temperatureto warm to room temperature
  2. temperatureAfter re-cooling to 0° C.
  3. customThe yellow precipitate that formed
  4. filtrationwas collected by vacuum filtration
  5. customAfter drying

Sources & evidence

ORD record
ord-c2929f08d2ec4724ad6b823a1b5a92f6
Source dataset
uspto-grants-2007_11
Patent number
US07297704B2

Reaction notes

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