1-Butanol → 1-(p-Nitroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride

HRID 543731Notes

Reaction equation

HRID 543731 reaction equation
C(OC(OCC)C[N:6]([C:16](=O)[CH3:17])[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][CH:8]=1)C.[ClH:22].[OH:23][C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][C:32]=1[OH:33])[CH2:27][CH2:28][NH2:29].C(O)CCC>O>[ClH:22].[N+:13]([C:10]1[CH:9]=[CH:8][C:7]([NH:6][CH2:16][CH:17]2[C:30]3[C:26](=[CH:25][C:24]([OH:23])=[C:32]([OH:33])[CH:31]=3)[CH2:27][CH2:28][NH:29]2)=[CH:12][CH:11]=1)([O-:15])=[O:14]

Participants

5

Reactant 3

HCID 2631-ButanolHCID 65340Dopamine HydrochlorideHCID 20460584N-(2,2-Diethoxyethyl)-N-(4-nitrophenyl)acetamide

Product 1

HCID 204605071-(p-Nitroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochlorideYield 84.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of N-acetyl-p-nitroanilinoacetaldehyde diethyl acetal (1 g), 3,4-dihydroxyphenethylamine hydrochloride (1 g), n-butyl alcohol (10 ml) and water (1.5 ml) was refluxed for 7 hours. In the course of the reaction, the above-mentioned acetal (2.5 g) was added to the mixture, twice in 0.5 g portions and five times in 0.3 g portions, one every hour. The reaction mixture was filtered and the filtrate was concentrated to dryness. The residue was pulverized by adding ether and the powder was collected by filtration, washed with ethyl acetate and water and dried to give 1-(p-nitroanilinomethyl)-6,7-dihydroxy-1,2,3,4-tetrahydroisoquinoline hydrochloride (1 g), mp 238° to 239° C. (dec).

Workup

  1. temperaturewas refluxed for 7 hours
  2. customIn the course of the reaction
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated to dryness
  5. additionby adding ether
  6. filtrationthe powder was collected by filtration
  7. washwashed with ethyl acetate and water
  8. customdried

Sources & evidence

ORD record
ord-075b6ccd0885482cb64c0dddc7033f47
Source dataset
uspto-grants-1984_05
Patent number
US04447436

Reaction notes

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