1,2-Dichloroethane → 2-(4-Methoxy-3-nitro-benzoylamino)-indane-2-carboxylic acid methyl ester

HRID 521468Notes

Reaction equation

HRID 521468 reaction equation
Cl.[CH3:2][O:3][C:4]([C:6]1([NH2:15])[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5].[CH3:16][O:17][C:18]1[CH:26]=[CH:25][C:21]([C:22](O)=[O:23])=[CH:20][C:19]=1[N+:27]([O-:29])=[O:28].CN1CCOCC1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl>CN(C=O)C>[CH3:2][O:3][C:4]([C:6]1([NH:15][C:22](=[O:23])[C:21]2[CH:25]=[CH:26][C:18]([O:17][CH3:16])=[C:19]([N+:27]([O-:29])=[O:28])[CH:20]=2)[CH2:14][C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH2:7]1)=[O:5]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 79724-MethylmorpholineHCID 666404-Methoxy-3-nitrobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 45074056methyl 2-amino-2,3-dihydro-1H-indene-2-carboxylate hydrochloride

Product 1

HCID 670766712-(4-Methoxy-3-nitro-benzoylamino)-indane-2-carboxylic acid methyl esterYield 65.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 2-amino-indane-2-carboxylic acid methyl ester hydrochloride (0.40 g, 1.77 mmol) and 4-methoxy-3-nitrobenzoic acid (0.35 g, 1.77 mmol) in 4 ml of DMF were added NMM (0.59 ml, 5.32 mmol), HOBT (0.31 g, 2.31 mmol) and EDC (0.44 g, 2.31 mmol). The mixture was stirred at 60° C. until LC/MS analysis showed complete conversion. The crude product was purified by silica gel chromatography (HEP/EA gradient) to give 0.43 g of the title compound.

Workup

  1. customThe crude product was purified by silica gel chromatography (HEP/EA gradient)

Sources & evidence

ORD record
ord-d7f7620cbc314ee49e160a2b6e65936e
Source dataset
uspto-grants-2016_05
Patent number
US09328071B2

Reaction notes

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