Ethylamine → HCID 57949760, compound

HRID 2427652Notes

Reaction equation

HRID 2427652 reaction equation
CO[C:3](=[O:14])[C:4]1[C:9]([Cl:10])=[CH:8][C:7]([Br:11])=[CH:6][C:5]=1[CH2:12]Br.C1COCC1.[CH2:20]([NH2:22])[CH3:21].C([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.CCCCCC.C(OCC)(=O)C>[Br:11][C:7]1[CH:6]=[C:5]2[C:4](=[C:9]([Cl:10])[CH:8]=1)[C:3](=[O:14])[N:22]([CH2:20][CH3:21])[CH2:12]2

Participants

8

Reactant 4

HCID 6341EthylamineHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 59512234Methyl 4-bromo-2-(bromomethyl)-6-chlorobenzoate

Product 1

HCID 57949760HCID 57949760, compoundYield 37%

Reagents, catalysts & solvents 3

HCID 1140TolueneSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 4-bromo-2-bromomethyl-6-chloro-benzoic acid methyl ester (0.684 g, 2.00 mmol), 2M THF solution of ethyl amine (1.3 mL, 2.6 mmol), and K2CO3 (0.552 g, 4.0 mmol) in toluene (5 mL) was heated with stirring at 100° C. for 2 h. Workup and silica gel column chromatography using 30% ethyl acetate in hexane afforded 5-bromo-7-chloro-2-ethyl-2,3-dihydro-isoindol-1-one (0.203 g, 37%). GC-MS: m/z 275 (M)+, 258 (M−27)+. 1H NMR (300 MHz, CDCl3): δ (ppm) 1.24 (t, 3H), 3.64 (q, 2H) 4.34 (s, 2H), 7.50 (s, 1H), 7.58 (s, 1H).

Workup

  1. temperaturewas heated

Sources & evidence

ORD record
ord-0fb5d2df2f7449e2b4518d5990952cc7
Source dataset
uspto-grants-2011_06
Patent number
US07968570B2

Reaction notes

Loading…