1-Naphthalenemethanamine → 4-Oxo-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid-(naphthalene-1-ylmethyl)-amide

HRID 322490Notes

Reaction equation

HRID 322490 reaction equation
[C:1]1([CH2:11][NH2:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[O:13]=[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:17]([C:24](O)=[O:25])[CH2:16][CH2:15]1>CN(C1C=CN=CC=1)C.C(Cl)Cl>[C:1]1([CH2:11][NH:12][C:24]([CH:17]2[C:18]3[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:14](=[O:13])[CH2:15][CH2:16]2)=[O:25])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 83551-NaphthalenemethanamineHCID 2532491,2,3,4-Tetrahydro-4-oxo-1-naphthoic acid

Product 1

HCID 227196674-Oxo-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid-(naphthalene-1-ylmethyl)-amide

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 1-naphthalenemethylamine (1.37 g, 7.2 mmol), 4-oxo-1,2,3,4-tetrahydronaphthalene-1-carboxylic acid (1.13 g, 7.2 mmol) ECD (2.87 g, 15 mmol), and DMAP (1.83 g, 15 mmol) in CH2Cl2 (20 mL) was stirred at room temperature. After 12 h, the reaction mixture was concentrated and the residue was purified by flash column chromatography (2-5% MeOH in CH3Cl to yield the product (2.29 g, 97% liht yellow solid, m.p. 155-156° C.).

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customthe residue was purified by flash column chromatography (2-5% MeOH in CH3Cl
  3. customto yield the product (2.29 g, 97% liht yellow solid, m.p. 155-156° C.)

Sources & evidence

ORD record
ord-759468f54e614c279f16fe414fa89104
Source dataset
uspto-grants-2001_04
Patent number
US06211241B1

Reaction notes

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