Hexamethylenetetramine → 2-Amino-1-(4-nitrophenyl)ethan-1-one hydrochloride

HRID 1024423Notes

Reaction equation

HRID 1024423 reaction equation
C1N2CN3CN(C2)C[N:2]1C3.Br[CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:14].C(Cl)[Cl:25]>>[ClH:25].[NH2:2][CH2:12][C:13]([C:15]1[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=1)=[O:14]

Participants

4

Reactant 3

HCID 4101HexamethylenetetramineHCID 6344DichloromethaneHCID 668402-Bromo-4'-nitroacetophenone

Product 1

HCID 27928012-Amino-1-(4-nitrophenyl)ethan-1-one hydrochlorideYield 72%

Procedure

Hexamethylenetetramine (20.1 g) was added to a solution of 2-bromo-1-(4-nitrophenyl)ethanone (step A product, 25 g) in DCM (250 ml) and the mixture was stirred for 1 hour. It was then filtered and the residue was dissolved in ethanolic HCl (40 mL HCl in 162 ml EtOH). The ethanolic solution was stirred for 3 hours and was left undisturbed for 2 days. The solution was filtered and the residue was washed with water and dried to yield 11.8 g (72%) of the title compound. 1HNMR (DMSO-d6, 300 MHz): δ 8.3 (bs, 3H), 8.38 (d, 2H), 8.27 (d, 2H), 4.68 (s, 2H).

Workup

  1. filtrationIt was then filtered
  2. dissolutionthe residue was dissolved in ethanolic HCl (40 mL HCl in 162 ml EtOH)
  3. stirringThe ethanolic solution was stirred for 3 hours
  4. waitwas left undisturbed for 2 days
  5. filtrationThe solution was filtered
  6. washthe residue was washed with water
  7. customdried

Sources & evidence

ORD record
ord-326f391185494cec9899d74fd2f8c182
Source dataset
uspto-grants-2014_05
Patent number
US08722901B2

Reaction notes

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