HCID 20329766, compound → HCID 20329768, compound

HRID 2058047Notes

Reaction equation

HRID 2058047 reaction equation
[N+:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[C:14]([O:16][C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)=[O:15])=[CH:6][CH:5]=1)([O-])=O>C(O)(=O)C.[Zn]>[ClH:23].[NH2:1][C:4]1[CH:13]=[C:12]2[C:7]([CH2:8][CH2:9][CH2:10][CH:11]2[C:14]([O:16][C:17]2[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=2)=[O:15])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 20329766HCID 20329766, compound

Product 1

HCID 20329768HCID 20329768, compound

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent2×

Procedure

A 330-mg portion of the p-chlorophenyl 7-nitro-1,2,3,4-tetrahydro-1-naphthoate obtained above was dissolved in 10 ml of acetic acid and the resulting solution was slowly added dropwise at room temperature to 10 ml of acetic acid containing 2 g of zinc dust. After 30 minutes the precipitates were removed by filtration and the filtrate was concentrated under reduce pressure. The residue was dissolved in ethyl acetate and washed with a 5% aqueous sodium hydrogen carbonate solution. The ethyl acetate layer was concentrated under reduced pressure. The residue was dissolved in diethyl ether and dry gaseous hydrogen chloride was introduced thereinto to obtain 290 mg of p-chlorophenyl 7-amino-1,2,3,4-tetrahydro-1-naphthoate hydrochloride having a melting point of 175°-177° C.

Workup

  1. customAfter 30 minutes the precipitates were removed by filtration
  2. concentrationthe filtrate was concentrated
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with a 5% aqueous sodium hydrogen carbonate solution
  5. concentrationThe ethyl acetate layer was concentrated under reduced pressure
  6. dissolutionThe residue was dissolved in diethyl ether
  7. additiondry gaseous hydrogen chloride was introduced

Sources & evidence

ORD record
ord-a0ded4e617e44f65a389d5097f919de8
Source dataset
uspto-grants-1980_07
Patent number
US04214093

Reaction notes

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