Benzoyl chloride → 2-((Phenyl)carbonyl)amino-7-nitrotetralin

HRID 2393561Notes

Reaction equation

HRID 2393561 reaction equation
[NH2:1][CH:2]1[CH2:11][CH2:10][C:9]2[C:4](=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[CH:7][CH:8]=2)[CH2:3]1.[C:15](Cl)(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C1COCC1.C([O-])([O-])=O.[K+].[K+].O>[C:16]1([C:15]([NH:1][CH:2]2[CH2:11][CH2:10][C:9]3[C:4](=[CH:5][C:6]([N+:12]([O-:14])=[O:13])=[CH:7][CH:8]=3)[CH2:3]2)=[O:22])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 2

HCID 7412Benzoyl chlorideHCID 232984217-Nitro-1,2,3,4-tetrahydronaphthalen-2-amine

Product 1

HCID 232984092-((Phenyl)carbonyl)amino-7-nitrotetralin

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 11430Potassium CarbonateSolvent

Procedure

To 2-amino-7-nitrotetralin (1.8 g, 9.39 mmol, derived from dibenzoyl-D-tartaric acid) in THF (50 ml) and 10% K2CO3 (100 ml) was added benzoyl chloride (1.2 ml, 10.1 mmol). After the addition was complete, the mixture was diluted with water to a volume of 250 ml. The precipatated solids were collected by filtration, washed with water and dried in vacuo: (2.8 g, 100%), m.p. 208°-209° C., [α]D +21.9° (c 0.33 DMSO).

Workup

  1. additionAfter the addition
  2. filtrationThe precipatated solids were collected by filtration
  3. washwashed with water
  4. customdried in vacuo

Sources & evidence

ORD record
ord-a31722b723264bcb9f0e6200e76b5d00
Source dataset
uspto-grants-1998_09
Patent number
US05807886

Reaction notes

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