Ammonia → HCID 13318640, compound

HRID 544340Notes

Reaction equation

HRID 544340 reaction equation
[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH:14]([N:19]=[N+:20]=[N-:21])[CH2:13][CH2:12][C:11]=2[C:10]=1[C:22]([O-:24])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH3:25]>CO>[CH2:1]([O:8][C:9]1[CH:18]=[CH:17][C:16]2[CH2:15][CH:14]([N:19]=[N+:20]=[N-:21])[CH2:13][CH2:12][C:11]=2[C:10]=1[C:22]([NH2:25])=[O:24])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86739411HCID 86739411, compound

Product 1

HCID 13318640HCID 13318640, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a still different procedure (Reaction Scheme E below), in which the order of steps is somewhat changed, the methyl dl-2-benzyloxy-6-azido-5,6,7,8-tetrahydro-1-naphthoate (XXV) can be treated with ammonia in methanol under pressure to yield the corresponding dl-2-benzyloxy-6-azido-5,6,7,8-tetrahydronaphthalene-1-carboxamide (XXXIX). Conversion of the azide group to an amino group with hydrazine and Raney nickel yields a dl-2-benzyloxy-6-amino-5,6,7,8-tetrahydronaphthalene-1-carboxamide (XXXXI). This compound can be treated directly with hydrogen in the presence of a palladium catalyst to remove the benzyl group and yield a compound according to formula Ib above wherein R2 and R3 are both hydrogen. Alternatively, the benzyloxy derivative can be alkylated with a lower aldehyde and sodium cyanoborohydride to yield a dl-2-benzyloxy-6-dialkylamino-5,6,7,8-tetrahydronaphthalene-1-carboxamide (XXXXI) which compound, upon treatment with hydrogen in the presence of a palladium catalyst, yields a compound of this invention (Ib) where R2 and R3 are individually Me, Et or n-Pr.

Workup

  1. customIn a still different procedure (Reaction Scheme E below)

Sources & evidence

ORD record
ord-7c9c9c55032444d9adc0919b5ac9efb1
Source dataset
uspto-grants-1984_05
Patent number
US04448990

Reaction notes

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