Trifluoroacetic acid methylene chloride → 4-(Aminomethyl)-N-(2-aminophenyl)benzamide

HRID 852973Notes

Reaction equation

HRID 852973 reaction equation
C([CH:8]([NH2:32])[C:9]1[CH:31]=[CH:30][C:12]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH:22]C(=O)OC(C)(C)C)=[O:14])=[CH:11][CH:10]=1)(OC(C)(C)C)=O.C(Cl)Cl.C(O)(C(F)(F)F)=O>>[NH2:32][CH2:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[NH2:22])=[O:14])=[CH:30][CH:31]=1

Participants

3

Reactant 2

HCID 21863450Trifluoroacetic acid methylene chlorideHCID 86601383HCID 86601383, compound

Product 1

HCID 588172504-(Aminomethyl)-N-(2-aminophenyl)benzamideYield 100%

Procedure

A solution of 391 (840 mg, 1.9 mmol) in 2:1 mixture of DCM/TFA (6 mL) was stirred at room temperature for 2 hours. The reaction mixture was concentrated in vacuo to afford the title compound as a mixture of the mono and di-TFA salt. (1.33 g, 100% yield). LRMS: (calc) 241.2; (found) 242.2 (M+H1).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-cdb6d2fcc5b5417080f06c2b2d5f11fc
Source dataset
uspto-grants-2007_08
Patent number
US07253204B2

Reaction notes

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