1-Naphthol → 1,1'-Dinaphthylamine

HRID 1833952Notes

Reaction equation

HRID 1833952 reaction equation
[C:1]1(O)[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:12]1([NH2:22])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[CH:15]=[CH:14][CH:13]=1.P(OC1C=CC=CC=1)(OC1C=CC=CC=1)OC1C=CC=CC=1>O>[CH:7]1[CH:6]=[C:5]2[CH:4]=[CH:3][CH:2]=[C:1]([NH:22][C:12]3[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:15]=[CH:14][CH:13]=3)[C:10]2=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 7540Triphenyl phosphiteHCID 86401-Naphthylamine

Product 1

HCID 2244801,1'-DinaphthylamineYield 93%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
220 °C

Procedure

144 parts of α-naphthol, 143 parts of α-naphthylamine and 15 parts of triphenyl phosphite are mixed and heated to 220° C. The elimination of water commences at this temperature and has ended when the internal temperature reaches 250° C. 18 parts of water are removed in the course of 10 hours. After distilling off excess α-naphthol and α-naphthylamine, 250 parts of 1,1'-dinaphthylamine, of melting point 97° - 102° C, are obtained at 256° - 257°/5 mm Hg. This corresponds to a yield of 93% of theory.

Workup

  1. customreaches 250° C
  2. custom18 parts of water are removed in the course of 10 hours
  3. distillationAfter distilling off excess α-naphthol and α-naphthylamine, 250 parts of 1,1'-dinaphthylamine
  4. customof melting point 97° - 102° C, are obtained at 256° - 257°/5 mm Hg

Sources & evidence

ORD record
ord-97849abc28884ad0b28ef2730a7a3baa
Source dataset
uspto-grants-1978_01
Patent number
US04067903

Reaction notes

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