Dimethylformamide → HCID 827252, compound

HRID 2250405Notes

Reaction equation

HRID 2250405 reaction equation
[C:1]1([C:15]([OH:17])=O)[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1.C[N:19](C=O)C.C(Cl)(=O)C(Cl)=O.[OH-].[NH4+]>C1COCC1>[C:1]1([C:15]([NH2:19])=[O:17])[C:14]2[C:5](=[CH:6][C:7]3[C:12]([CH:13]=2)=[CH:11][CH:10]=[CH:9][CH:8]=3)[CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 14923Ammonium HydroxideHCID 65578Oxalyl chlorideHCID 1507891-Anthracenecarboxylic Acid

Product 1

HCID 827252HCID 827252, compoundYield 103.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of anthracene-1-carboxylic acid (2.5 g, 11.26 mmol) in THF (30 ml) was added DMF (1.75 ml, 22.52 mmol). The solution was cooled to 0° C. and oxalyl dichloride (2M in CH2Cl2, 22.5 ml, 45 mmol) was added dropwise. The reaction solution was stirred at room temperature for 2 hours and then was cannulated into a solution of concentrated ammonium hydroxide (25 ml) in a 3-necked flask cooled at 0° C. The reaction mixture was allowed to warm to room temperature and stirred for 24 hours. The white precipitate was filtered and washed with water to give anthracene-1-carboxylic acid amide as an off-white solid (2.58 g, 100% yield). LC/MS (m/z 222.15 (M+H)+); HPLC (Column: Shimadzu VP-0DS, C-18 Ballistic; 10-90% aq CH3OH/0.1% H3PO4, same for compounds hereafter unless noted) Rt: 2.872 min.

Workup

  1. temperaturecooled at 0° C
  2. temperatureto warm to room temperature
  3. stirringstirred for 24 hours
  4. filtrationThe white precipitate was filtered
  5. washwashed with water

Sources & evidence

ORD record
ord-6129cf16fd8b43f6b5cc76f31042d832
Source dataset
uspto-grants-2008_01
Patent number
US07317024B2

Reaction notes

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