Hydrochloric Acid → 4-Fluoro-5-(pyrrolidin-1-yl)-1,2-phenylenediamine

HRID 1004584Notes

Reaction equation

HRID 1004584 reaction equation
[N+:1]([C:4]1[CH:10]=[C:9]([F:11])[C:8]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:7][C:5]=1[NH2:6])([O-])=O.Cl>[Fe].C(O)C>[F:11][C:9]1[C:8]([N:12]2[CH2:16][CH2:15][CH2:14][CH2:13]2)=[CH:7][C:5]([NH2:6])=[C:4]([NH2:1])[CH:10]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 29587482-Nitro-4-fluoro-5-(pyrrolidin-1-yl)aniline

Product 1

HCID 187927834-Fluoro-5-(pyrrolidin-1-yl)-1,2-phenylenediamineYield 97.8%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 702EthanolSolvent

Procedure

The nitroaniline derivative (5.0 g, 0.022 mol) (obtained in step 1 above) was reduced using Fe powder (12.6 g, 0.22 mol), conc. HCl (33 mL) and ethanol (33 mL) as described in preparation 10 (step 2) to yield 4-fluoro-5-(pyrrolidin-1-yl)-1,2-phenylenediamine (4.2 g, 97%) as viscous oil. IR (Neat) 3340, 1524 cm-1 ; 1H NMR (CDCl3) δd 1.93 (m, 4H, (CH2)2), 3.24 (m, 4H, N(CH2)2), 3.56 (brs, 4H, 2×NH2), 6.18 (d, J=7.2 Hz, 1H), 6.48 (d, J=13.2 Hz, 1H); Mass (m/z) 195 (M+.).

Workup

  1. customas described in preparation 10 (step 2)

Sources & evidence

ORD record
ord-b46afbc171b94574a57d51db5cd8c78c
Source dataset
uspto-grants-2000_04
Patent number
US06051570

Reaction notes

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