Hydrochloric Acid → HCID 178506259, compound

HRID 1399946Notes

Reaction equation

HRID 1399946 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-adb941bc526a421ba3b95e92bd507d51
Source dataset
uspto-grants-2014_12
Patent number
US08906909B2

Reaction notes

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