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Ethylenediamine → N'-(2-chlorophenyl)ethane-1,2-diamine

HRID 705
Notes
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Reaction equation

HRID 705 reaction equation
Clc1ccccc1Br.NCCN>CC(=O)O.CC(=O)O.CC(C)(C)[O-].Cc1ccc(P(c2ccc(C)cc2)c2ccc(C)cc2)cc1.Cc1ccccc1.[Na+].[Pd]>NCCNc1ccccc1Cl
ParticipantsConditionsProcedureSources & evidenceReaction notes

Participants

7

Reactant 2

HCID 3301EthylenediamineHCID 127541-Bromo-2-chlorobenzene

Product 1

HCID 12666392N'-(2-chlorophenyl)ethane-1,2-diamineYield 0%

Reagents, catalysts & solvents 4

HCID 23676156Sodium t-butoxideReagentHCID 13956Phosphine, tris(4-methylphenyl)-CatalystHCID 4144353Palladium (II) acetateCatalystHCID 1140TolueneSolvent

Conditions

Temperature
140 °C

Procedure

Ref: R2239 To a mixture of 1-bromo-2-chlorobenzene (0.824 g, 4.30 mmol), tri-p- tolylphosphine (0.262 g, 0.86 mmol), sodium 2-methylpropan-2-olate (0.414 g, 4.30 mmol), diacetoxypalladium (0.097 g, 0.43 mmol) in toluene (4 mL) was added ethane-1,2-diamine (1.293 g, 21.52 mmol). The mixture was heated with microwave at 140 °C for 1 h. No product was formed.

Sources & evidence

ORD record
ord-5911a740f60145b0bc355f2a886b772f
Source dataset
750 AstraZeneca ELN dataset
Original link
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Reaction notes

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On this pageParticipantsConditionsProcedureSources & evidenceReaction notes