Hydrochloric Acid → HCID 13364595, compound

HRID 2118925Notes

Reaction equation

HRID 2118925 reaction equation
OC1C=C(OC(CCCC2C=CC=CC=2)C)C=C2C=1C(C(OC1C=CC([N+]([O-])=O)=CC=1)=O)CC(C)(C)C2.CN.Cl.C[NH-].C[NH:44][C:45]([CH:47]1[C:56]2[C:51](=[CH:52][C:53]([O:58][CH:59]([CH2:61][CH2:62][CH2:63][C:64]3[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=3)[CH3:60])=[CH:54][C:55]=2[OH:57])[CH2:50][C:49]([CH3:71])([CH3:70])[CH2:48]1)=[O:46]>O1CCCC1>[OH:57][C:55]1[CH:54]=[C:53]([O:58][CH:59]([CH2:61][CH2:62][CH2:63][C:64]2[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=2)[CH3:60])[CH:52]=[C:51]2[C:56]=1[CH:47]([C:45]([NH2:44])=[O:46])[CH2:48][C:49]([CH3:71])([CH3:70])[CH2:50]2

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6329MethylamineHCID 21952893MethylamideHCID 54120477HCID 54120477, compoundHCID 54176583HCID 54176583, compound

Product 1

HCID 13364595HCID 13364595, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Reaction of 0.55 g. (1.1 mmole) p-nitrophenyl 8-hydroxy-3,3-dimethyl-6-(5-phenyl-2-pentyloxy)tetralin-1-carboxylate in 10 ml. tetrahydrofuran with an excess of methylamine (gas) at room temperature, pouring the resulting mixture into 10% hydrochloric acid, extracting with ethyl acetate and work-up in the usual manner affords 0.50 g. of the N-methyl amide: N-methyl 8-hydroxy-3,3-dimethyl-6-(5-phenyl-2-pentyloxy)tetralin-1-carboxamide as a foam. 1H-NMR (CDCl3) ppm (delta): 0.8 (s, 3H), 1.0 (s, 3H), 1.2 (d, 4H), 1.7 (m, 6H), 2.53 (m, 6H), 3.6 (m, 1H), 4.23 (m, NH), 6.2 (d, 2H), 7.13 (s, 5H).

Workup

  1. customReaction of 0.55 g
  2. extractionextracting with ethyl acetate
  3. customaffords 0.50 g

Sources & evidence

ORD record
ord-380a9605514344f2847f0efeb62ef73e
Source dataset
uspto-grants-1987_07
Patent number
US04680404

Reaction notes

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