1-Naphthalenecarbonyl chloride → HCID 68578556, compound

HRID 642674Notes

Reaction equation

HRID 642674 reaction equation
[C:1]1([C:11](Cl)=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[Al+3].[Cl-].[Cl-].[Cl-].[CH2:18]([O:20][C:21]([C:23]1[NH:24][C:25]2[C:30]([CH:31]=1)=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH3:19]>ClCCCl>[CH2:18]([O:20][C:21]([C:23]1[NH:24][C:25]2[C:30]([C:31]=1[C:11]([C:1]1[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[CH:4]=[CH:3][CH:2]=1)=[O:12])=[CH:29][CH:28]=[CH:27][CH:26]=2)=[O:22])[CH3:19]

Participants

5

Reactant 3

HCID 701461-Naphthalenecarbonyl chlorideHCID 73125Ethyl indole-2-carboxylateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 68578556HCID 68578556, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

1. To a solution of naphthalene-1-carbonyl chloride (3.43 g) and AlCl3 (2.40 g) in 1,2-dichloroethane (7 ml) was added at 0° C. a solution of 1H-indole-2-carboxylic acid ethyl ester (1.70 g) in 1,2-dichloroethane (7 ml) and the mixture was heated at reflux temperature for 2 h. The mixture was partitioned between ice cold water and AcOEt, the organic layer was washed with aqueous Na2CO3, dried and evaporated. The residue was chromatographed on silica (n-heptane/AcOEt, 5:1) to give 3-(naphthalene-1-carbonyl)-1H-indole-2-carboxylic acid ethyl ester as pale yellow solid. MS: 344.1 ([M+H]+).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux temperature for 2 h
  3. customThe mixture was partitioned between ice cold water and AcOEt
  4. washthe organic layer was washed with aqueous Na2CO3
  5. customdried
  6. customevaporated
  7. customThe residue was chromatographed on silica (n-heptane/AcOEt, 5:1)

Sources & evidence

ORD record
ord-b15422611ef24e1c8a1025b1ec55dc2f
Source dataset
uspto-grants-2010_04
Patent number
US07696240B2

Reaction notes

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