Oxalyl chloride → 3-Cyano-5,6,7,8-tetrahydronaphthalene-1-carbonyl chloride

HRID 2185889Notes

Reaction equation

HRID 2185889 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([C:13]([OH:15])=O)[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2].C(Cl)(=O)C([Cl:19])=O>C(Cl)Cl.CN(C=O)C>[C:1]([C:3]1[CH:4]=[C:5]([C:13]([Cl:19])=[O:15])[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][C:11]=2[CH:12]=1)#[N:2]

Participants

5

Reactant 2

HCID 65578Oxalyl chlorideHCID 224526443-Cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid

Product 1

HCID 224526673-Cyano-5,6,7,8-tetrahydronaphthalene-1-carbonyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarboxylic acid (0.207 g, 1.03 mmol) in DCM (5 mL) was added oxalyl chloride (0.112 mL, 1.29 mmol) and 1 drop of DMF. The mixture was stirred at room temperature for 2 h., the solvent was removed in vacuo and the 3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarbonyl chloride was used without purification.

Workup

  1. customthe solvent was removed in vacuo
  2. customthe 3-cyano-5,6,7,8-tetrahydro-1-naphthalenecarbonyl chloride was used without purification

Sources & evidence

ORD record
ord-055cebf526db482ba19956c73b9b5f72
Source dataset
uspto-grants-2002_06
Patent number
US06403601B1

Reaction notes

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