Ammonium Hydroxide → 7-Nitro-1,2,3,4-tetrahydroisoquinoline-1-acetamide

HRID 583244Notes

Reaction equation

HRID 583244 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH:11]2[CH2:14][C:15]#[N:16])=[CH:6][CH:5]=1)([O-:3])=[O:2].[OH-:17].[NH4+]>S(=O)(=O)(O)O>[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][NH:10][CH:11]2[CH2:14][C:15]([NH2:16])=[O:17])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 215843867-Nitro-1,2,3,4-tetrahydroisoquinoline-1-acetonitrile

Product 1

HCID 215843917-Nitro-1,2,3,4-tetrahydroisoquinoline-1-acetamideYield 89%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

To cold concentrated sulfuric acid (100 ml) was added, in a single portion, 7-nitro-1,2,3,4-tetrahydroisoquinoline-1-acetonitrile (12.6 g, 58.0 mmol). The reaction mixture was stirred for 6 h at that temperature after which time all the starting material had dissolved. The reaction mixture was poured on ice and the solution made basic with concentrated ammonium hydroxide at such a rate as to control the exotherm. The precipitated product was collected, washed with copious amounts of water, and air-dried to give the title compound as a red solid (12.1 g, 89%), m.p. 246-7° C. (dec.).

Workup

  1. dissolutionhad dissolved
  2. additionThe reaction mixture was poured on ice
  3. customThe precipitated product was collected
  4. washwashed with copious amounts of water
  5. customair-dried

Sources & evidence

ORD record
ord-0d20e0fce5ae42bab085ca1b7a1e3b4b
Source dataset
uspto-grants-1999_07
Patent number
US05929085

Reaction notes

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