1,2-Dichloroethane → HCID 23072474, compound

HRID 1182474Notes

Reaction equation

HRID 1182474 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:19]([OH:21])=O)=[O:12].C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.Cl.[O:37]([NH2:39])[CH3:38].C(N(CC)CC)C>CN(C=O)C>[CH3:38][O:37][NH:39][C:19](=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][C:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)=[O:12]

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 8471TriethylamineHCID 757711-HydroxybenzotriazoleHCID 521874O-Methylhydroxylamine hydrochlorideHCID 109459918-(2-NAPHTHYL)-8-OXOOCTANOIC ACID

Product 1

HCID 23072474HCID 23072474, compoundYield 56%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 7-(2-naphthoyl)heptanoic acid 50 g (500 mg, 1.76 mmol) in DMF (10 mL) were added HOBT (309 mg, 2.29 mmol) and EDC (504 mg, 2.64 mmol). The mixture was stirred at room temperature for 1 hour, after which methoxylamine-HCl (176 mg, 2.11 mmol) and triethylamine (300 μL, 2.11 mmol) were added and the solution was stirred at room temperature for 16 hours, then at 45° C. for 2 hours. The DMF was evaporated under high vacuum, deionized water was added, and the mixture was extracted with ethyl acetate (2×30 mL). The combined organic layers were washed with saturated sodium bicarbonate (10 mL), washed with brine (10 mL), and dried (MgSO4). The solvents were removed in vacuo and the title compound 64 (308 mg, 56%) was isolated by recrystallization from acetone. 1H NMR (400 MHz, 5:1 CDCl3:CD3OD): 8.37 (s, 1H), 7.89 (m, 2H), 7.78 (m, 2H), 7.48 (m, 2H), 3.59 (s, 3H), 3.01 (t, J=7.3 Hz, 2H), 1.96 (t, J=7.3 Hz, 2H), 1.67 (m, 2H), 1.54 (m, 2H), 1.31 (m, 4H).

Workup

  1. stirringthe solution was stirred at room temperature for 16 hours
  2. waitat 45° C. for 2 hours
  3. customThe DMF was evaporated under high vacuum
  4. additionwas added
  5. extractionthe mixture was extracted with ethyl acetate (2×30 mL)
  6. washThe combined organic layers were washed with saturated sodium bicarbonate (10 mL)
  7. washwashed with brine (10 mL)
  8. dry with materialdried (MgSO4)
  9. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-8270867711d5422b8e77de16d0643d33
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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