Hydrochloric Acid → HCID 178506259, compound

HRID 1255819Notes

Reaction equation

HRID 1255819 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([NH2:8])=[CH:6][CH:7]=1.[C:10](O)([C:12]([F:15])([F:14])[F:13])=O.Cl>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]2[NH:8][C:10]([C:12]([F:15])([F:14])[F:13])=[N:9][C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 3235934-Bromobenzene-1,2-diamine

Product 1

HCID 178506259HCID 178506259, compoundYield 61.3%

Procedure

A mixture of 4-bromobenzene-1,2-diamine (3.0 g, 16.0 mmol), TFA (9.5 mL, 128.3 mmol) and aq. HCl (3 M, 32 mL) was heated to reflux overnight. The reaction mixture was concentrated and purified by column chromatography to afford the titled compound (2.60 g, 60%). LCMS: 265.0 [M+1]+. 1HNMR (400 MHz, DMSO-d6): δ 7.52 (dd, J=8.8 Hz, 1.2 Hz, 1H), 7.69 (d, J=8.4 Hz, 1H), 7.95 (s, 1H), 14.20 (br, 1H).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by column chromatography

Sources & evidence

ORD record
ord-25a171be88a4444b93ec373434dc9922
Source dataset
uspto-grants-2013_06
Patent number
US08461157B2

Reaction notes

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