Triethylamine → 1,2-Naphthalenediamine

HRID 2306108Notes

Reaction equation

[NH2:1][C:2]1[C:11]2[C:6](=[C:7](N)[CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.CC[N:15](CC)CC>>[C:2]1([NH2:1])[C:3]([NH2:15])=[CH:4][CH:5]=[C:6]2[C:11]=1[CH:10]=[CH:9][CH:8]=[CH:7]2

Participants

Reactant 2

HCID 8471Triethylamine

HCID 167201,5-Diaminonaphthalene

Product 1

HCID 136481,2-NaphthalenediamineYield 76%

Procedure

1″,5″-[Bis-(4′-O-demethyl-4β-N-4-desoxypodophyllotoxin)] naphthalene diamine (4b) was prepared according to the method described earlier, employing 1,5-diamino naphthalene (80 mg, 0.5 mmol), Bu4N30I−(185 mg, 0.5 mmol), Et3N (150 mg, 1.5 mmol) and 4′-O-demethyl-4β-bromo-4-desoxy podophyllotoxin (462 mg, 1.0 mmol) to give the product in 76% yield. Spectral data: 1H NMR (CDCl3); 7.22-7.28 (d, 2H), 7.10-7.19 (t, 2H), 6.73 (S, 2H), 6.58 (S, 2H), 6.50 6.55 (d, 2H), 6.33 (S, 4H), 5.98 (ABq, 4H), 5.34 (S, 2H), 4.87 (br, 2H), 4.63-4.70 (d, 2H), 4.52-4.59 (d, 2H), 4.36-4.48 (t, 2H), 3.85-3.95 (d, 2H), 3.82 (3, 6H), 3.20-3.31(dd, 2H), 2.98-3.16 (m, 2H); FAB MS: m/z 922 (M+); mp. 238-240° C.

Workup

customto give the product in 76% yield

Sources & evidence

ORD record: ord-562a4e8265d84bf19caaeabd5273b1e0
Source dataset: uspto-grants-2002_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06441198B1

Reaction notes

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