Water → 2-Amino-5-iodobenzonitrile

HRID 853749Notes

Reaction equation

HRID 853749 reaction equation
[I:1]Cl.[NH2:3][C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[C:6]#[N:7].O>CC(O)=O>[NH2:3][C:4]1[CH:11]=[CH:10][C:9]([I:1])=[CH:8][C:5]=1[C:6]#[N:7]

Participants

5

Reactant 3

HCID 962WaterHCID 24640Iodine chlorideHCID 729132-Aminobenzonitrile

Product 1

HCID 99648032-Amino-5-iodobenzonitrile

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

A solution of iodine monochloride (16.7 g, 0.1 mol) in glacial AcOH (30 mL) as added dropwise over 15 min to a stirred solution of 2-aminobenzonitrile (11.8 g, 0.1 mol) in glacial AcOH (125 mL) at room temperature. The mixture was stirred for 3 h and then poured into H2O (1000 mL). The resulting pinkish-brown solid was filtered, washed with H2O, and dried in vacuo. Crystallization from cyclohexane-toluene (9:1) gave 2-amino-5-iodobenzonitrile (9) as translucent plates (14.9 g, 64%): mp 85-86° C. (lit. 85-86° C.); 1H NMR (CDCl3) δ 7.60 (d, J=1.6 Hz, 1H, H-6), 7.57 (dd, J=9.2 Hz, 1.6 Hz, 1H, H-4), 6.53 (d, J=9.2 Hz, 1H, H-3), 4.45 (br s; 2H, NH2). The product was used directly in the next reaction (Step 2).

Workup

  1. filtrationThe resulting pinkish-brown solid was filtered
  2. washwashed with H2O
  3. customdried in vacuo
  4. customCrystallization from cyclohexane-toluene (9:1)

Sources & evidence

ORD record
ord-e2ca1eae18c04643aaf77fe206bed96c
Source dataset
uspto-grants-2007_08
Patent number
US07256197B2

Reaction notes

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