Dimethylformamide → HCID 59696618, compound

HRID 2099298Notes

Reaction equation

HRID 2099298 reaction equation
Cl[C:2]1[C:11]([C:12]([OH:14])=[O:13])=[CH:10][C:9]2[C:4](=[CH:5][C:6]([Cl:15])=[CH:7][CH:8]=2)[N:3]=1.[N-:16]=[N+:17]=[N-:18].[Na+].CN(C=O)C>O.[Na+].[Cl-]>[Cl:15][C:6]1[CH:5]=[C:4]2[C:9]([CH:10]=[C:11]([C:12]([OH:14])=[O:13])[C:2]3[N:3]2[N:16]=[N:17][N:18]=3)=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 33557Sodium AzideHCID 24266067HCID 24266067, compound

Product 1

HCID 59696618HCID 59696618, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 5234Sodium ChlorideSolvent

Conditions

Temperature
70 °C

Procedure

To a dry reaction vial with a screw cap was placed 2,7-dichloroquinoline-3-carboxylic acid (0.241 g, 1 mmol), sodium azide (0.078 g, 1.2 mmol) and dry DMF (3 mL) and shaken at 65-75° C. for a period of 24 h. The reaction mixture was diluted with water (100 mL), saturated with NaCl, the resulting solid was filtered and dried to give 0.100 g (41%) of the carboxytetrazole 5. TLC Rf: 0.06 (20% MeOH/EtOAc); 1H NMR (DMSO d6+CDCl3): δ 8.71 (bs, 1H), 8.60 (s, 1H), 8.30 (d, 1H, J=7.8 Hz), 7.79 (d, 1H, J=7.5 Hz); LCMS (ret. time): 21.28; MS (m/z): 249 (MH+).

Workup

  1. customTo a dry reaction vial with a screw
  2. customcap
  3. filtrationthe resulting solid was filtered
  4. customdried

Sources & evidence

ORD record
ord-e1889aa43a2d4a7d8da355a5922fc3a3
Source dataset
uspto-grants-2009_08
Patent number
US07569580B2

Reaction notes

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